Herbicidal sulfonamides

ABSTRACT

This invention relates to a novel class of sulfonamides and their use as herbicides and plant growth regulants.

This application is a divisional application of application Ser. No. 395,781, filed July 12, 1982, now U.S. Pat. No. 4,491,467, which in turn is a continuation-in-part of application Ser. No. 295,247, filed Aug. 24, 1981, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to a novel class of sulfonamides and their use as herbicides and plant growth regulants.

U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula: ##STR1## wherein

R₁ is ##STR2##

R₃ and R₆ are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH₃ S(O)_(n) -- or CH₃ CH₂ S(O)_(n) --;

R₄ is hydrogen, fluorine, chlorine, bromine or methyl;

R₅ is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;

R₇ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom;

R₈ is hydrogen, methyl, chlorine or bromine;

R₉ and R₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; and

Y is methyl or methoxy; or their agriculturally suitable salts; provided that:

(a) when R₅ is other than hydrogen, at least one of R₃, R₄, R₆ and R₇ is other than hydrogen and at least two of R₃, R₄, R₆ and R₇ must be hydrogen;

(b) when R₅ is hydrogen and all of R₃, R₄, R₆ and R₇ are other than hydrogen, then all of R₃, R₄, R₆ and R₇ must be either chlorine or methyl; and

(c) when R₃ and R₇ are both hydrogen, at least one of R₄, R₅ or R₆ must be hydrogen.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR3## wherein

R₁ and R₂ may independently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms.

U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR4## wherein

R₁ is hydrogen or lower saturated aliphatic acyl; and

R₂ is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.

The disclosed compounds are said to provide control of crabgrass, cress, endive, closer and Poa annua.

French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR5## wherein R=H, halogen, CF₃ or alkyl.

Logemann et al., Chem. Ab., 53, 18052g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR6## wherein R is butyl, phenyl or ##STR7## and R₁ is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR8## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.

Substituted-pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR9## wherein R=H or CH₃.

Unexamined European Pat. No. 7687 discloses, among others, herbicidal sulfonylures of the general structure: ##STR10## where

R is H, alkyl, alkenyl, aryl, etc.;

R₆ is H or alkyl; or

R and R₆ can be taken together to form --(CH₂)₄, --(CH₂)₅ --, --(CH₂)₆ --, --CH₂ CH₂ OCH₂ CH₂ -- or --CH₂ CH₂ N(CH₃)CH₂ CH₂ --.

U.S. Ser. No. 209,307, filed Nov. 24, 1980, discloses, among others, herbicidal sulfonylureas of the general structure: ##STR11## where

R is as disclosed in U.S. Ser. No. 029,281, now abandoned; and

R₆ is ##STR12##

The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.

SUMMARY OF THE INVENTION

This invention relates to compounds of Formula I and their agriculturally suitable salts, suitable agricultural compositions containing them and their method of use as general and/or selective pre-emergence and/or post-emergence herbicides and as plant growth regulants: ##STR13## wherein

A is a five- or six-membered aromatic heterocycle, a five- or six-membered dihydroaromatic heterocycle or a six-membered tetrahydroaromatic heterocycle which contains 1-4 heteroatoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms, and/or 0-4 nitrogen atoms; the heterocycles may be optionally substituted with 1-4 CH₃, 1-2 OCH₃, 0-1 SCH₃, 0-1 Cl, 0-1 N(CH₃)₂, or 0-1 CN groups;

R is H or CH₃ ;

R₁ is H, F, Cl, Br, CH₃, OCH₃, CF₃ or NO₂ ;

R₂ is H or CH₃ ;

R₃ is H or CH₃ ;

R₄ is ##STR14##

X is CH₃, OCH₃ or Cl;

Y is H, CH₃, C₂ H₅, OCH₃, OC₂ H₅, CH₂ OCH₃, NH₂, NHCH₃ or N(CH₃)₂ ;

Y₁ is H, Cl, CH₃ or OCH₃ ; and

Z is CH, CCH₃ or N

provided that

(1) the bond between N--R and A is attached to a nitrogen or carbon atom of A;

(2) when A is a thiophene or furan ring, the bond between NR and A is not at the 2- or 5-position of the heterocycle; and

(3) when X is Cl, then Z is CH and Y is CH₃, OCH₃, NH₂, NHCH₃ or N(CH₃)₂.

Preferred for higher herbicidal activity and/or more favorable ease of synthesis are:

(1) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered aromatic heterocycle containing one to three nitrogen atoms;

(2) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered dihydroaromatic heterocycle containing two nitrogen atoms;

(3) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one to four nitrogen atoms;

(4) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one or two nitrogen atoms and one oxygen or one sulfur atom;

(5) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered aromatic heterocycle containing one oxygen or one sulfur atom;

(6) Compounds of Formula I wherein A is an unsubstituted or substituted five-membered dihydroaromatic heterocycle containing one nitrogen atom and optionally one heteroatom selected from nitrogen, oxygen or sulfur;

(7) Compounds of Formula I wherein A is an unsubstituted or substituted six-membered tetrahydroaromatic heterocycle containing one nitrogen atom and optionally one heteroatom selected from nitrogen, oxygen or sulfur;

(8) Compounds of Preferred (1)-(7) wherein ##STR15##

Y is CH₃ or OCH₃ ; and

Z is CH or N;

(9) Compounds of Preferred (8) wherein A is unsubstituted or optionally substituted with 0-4 CH₃ or 0-2 OCH₃ groups;

(10) Compounds of Preferred (9) wherein A is a pyridine, a pyrimidine or a 1,3,5-triazine;

(11) Compounds of Preferred (9) wherein A is a pyrrole, an imidazole, a pyrazole, or a 1,2,4-triazole;

(12) Compounds of Preferred (9) wherein A is an isoxazole, an oxazole, a 1,3,4-oxadiazole, a thiazole, a 1,2,3-thiadiazole, or a 1,3,4-thiadiazole;

(13) Compounds of Preferred (9) wherein A is a 4,5-dihydroimidazole, a 4,5-dihydroisoxazole, a 4,5-dihydrooxazole, a 4,5-dihydropyrazole, or a 4,5-dihydrothiazole;

(14) Compounds of Preferred (9) wherein A is a tetrahydropyrimidine, a tetrahydro-1,2,-oxazine, a tetrahydrol,3-oxazine, or a tetrahydro-1,3-thiazine;

(15) Compounds of Preferred (10)-(14) wherein R, R₁, R₂ and R₃ are H, and A is unsubstituted, or, optionally substituted with one methyl group.

Specifically Preferred for highest herbicidal activity and/or most favorable ease of synthesis are:

2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(4,6-dimethylpyrimidin-2-yl)benzamide, m.p. 198°-199°;

2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(2-pyridinyl)benzamide, m.p. 206°-207°;

2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminocarbonyl]-N-(1,2,4-triazol-3-yl)benzamide, m.p. 226°-230°;

2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1-methyl-1H-pyrazol-3-yl)benzamide, m.p. 194°-197°;

2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(thiazol-2-yl)benzamide, m.p. 185°-187°;

2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1,3,4-thiadiazol-2-yl)benzamide, m.p. 172°-173°;

N-(3,4-dimethylisoxazol-5-yl)-2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzamide, m.p. 149°-151°.

Synthesis

The compounds of Formula I can be prepared from the corresponding esters by reaction with the heterocyclic amine III in the presence of an equivalent amount of trimethylaluminum according to Equation 1. ##STR16##

According to the procedure of A. Basha, M. Lipton, and S. W. Weinreb, Tetrahedron Letters, 4171 (1977), the heterocyclic amine and the trimethylaluminum are mixed in methylene chloride, followed by the addition of a methyl ester of Formula II. The mixture is then heated at reflux for 12 to 24 hours.

The product can be isolated by addition of aqueous hydrochloric acid to decompose and dissolve the aluminum complexes and salts. Direct filtration of the precipitate or separation of the methylene chloride phase followed by evaporation yields the desired product which may be purified by crystallization or column chromatography.

The preparation of esters of Formula II is described in European Patent Application No. 7687.

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by treating compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g. hydroxide, alkoxide, carbonate or hydride) quaternary amine salts can be made by similar techniques. Detailed examples of such techniques are given in U.S. Pat. No. 4,127,405, the disclosure of which is herein incorporated by reference.

The compounds of this invention and their preparaton are further illustrated by the following examples wherein temperatures are given in degrees centigrade and all parts are by weight unless otherwise indicated.

EXAMPLE 1 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(4,6-dimethylpyrimidin-2-yl)benzamide

To 1.44 g of trimethylaluminum (10 ml of a 2M solution of trimethylaluminum in toluene) in 100 ml of methylene chloride was added 2.5 g of 2-amino-4,6-dimethylpyrimidine with stirring at ambient temperature. To this mixture was added 4.0 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and the solution refluxed for 18 hours. The reaction mixture was then treated with aqueous hydrochloric acid and the precipitated product was found to be nearly pure by thin layer chromatography (TLC) on silica gel with an eluting solvent of ethyl acetate. Trituration of the solid with methylene chloride resulted in pure product (1.8 g); m.p. 198°-199° C.; IR: 3200 cm⁻¹, NH, 1720 cm⁻¹ sulfonylurea carbonyl, 1700 cm⁻¹ amide carbonyl.

NMR: 2.2 ppm s, 6H, CH₃ on pyrimidine, 3.9 ppm s, 6H, OCH₃ on pyrimidine, 5.8 ppm, s, 1H proton in 5-position on the dimethoxypyrimidine, 6.7 ppm s, 1H, proton in 5-position of dimethylpyrimidine, 7.4-7.8 ppm and 8.0-8.4 ppm M, 4H, aromatic protons.

EXAMPLE 2 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(2-pyridinyl)benzamide

To a slurry of 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide in 100 ml of methylene chloride was added by syringe 10 of a 2M solution of trimethylaluminum in toluene (1.44 g of Al(CH₃)₃). Evolution of methane gas was seen and the solution became homogeneous. 2-Aminopyrimidine (1.9 g) was then added and the mixture was heated at reflux for 18 hours. The reaction mixture was then treated with aqueous hydrochloric acid and the precipitated product was purified by trituration in methylene chloride, 1.35 g, m.p. 206°-207° C., IR: 1710 cm⁻¹ sulfonylurea carbonyl, 1680 cm⁻¹ amide carbonyl.

NMR: in TFA, 2.8 ppm, CH₃ on pyrimidine, 4.3 ppm, OCH₃ on pyrimidine, 6.8 ppm, proton in 5-position of pyrimidine, 7.8-8.0 ppm and 8.4-8.6 ppm, aromatic protons.

EXAMPLE 3 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1,2,4-triazol-3-yl)benzamide

To a slurry of 4.0 g of N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide in 100 ml of methylene chloride was added by syringe 10 ml of a 2M solution of trimethylaluminum in toluene (1.44 g of Al(CH₃)₃). Evolution of methane gas was seen. 3-Amino-1,2,4-triazole (1.7 g) was then added and the mixture was heated at reflux for 18 hours. The reaction mixture was then treated with aqueous hydrochloric acid and the precipitated product was purified by trituration in methylene chloride, 0.63 g, m.p. 176°-179° C. NMR in TFA 2.9 ppm s, CH₃ on triazine, 4.4 ppm s, OCH₃ on triazine, 7.8-8.0 ppm and 8.2-8.5 ppm M, aromatic.

EXAMPLE 4 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(thiazol-2-yl)benzamide

To a solution of 2-aminotriazole (2.1 g) in 100 ml of methylene chloride was added 10 ml of a 2M solution in toluene of trimethylaluminum (1.44 g of Al(CH₃)₃) by syringe. Evolution of methane gas was seen and the solution became homogeneous. To this mixture was added 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and the homogeneous solution was heated at reflux for 18 hours. The reaction mixture was then heated with aqueous hydrochloric acid and the precipitated product isolated by filtration, 1.42 g, m.p. 185°-187° C. IR: 1690 cm⁻¹ and 1700 cm⁻¹ unresolved double carbonyl, NMR: in TFA 2.7 ppm s, CH₃ pyrimidine, 4.2 ppm s, OCH₃ on pyrimidine, 6.7 ppm s, proton in 5-position on pyrimidine, 7.8-8.0 ppm and 8.4-8.5 ppm M, aromatic, 7.6, 7.7 ppm D, thiazole.

EXAMPLE 5 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-N-(1,3,4-thiadiazol-2-yl)benzamide

To a solution of 2-amino-1,3,4-thiadiazole (2.1 g) in 100 ml of methylene chloride was added 10 ml of a 2M solution in toluene of trimethylaluminum (1.44 g of Al(CH₃)₃) by syringe. Evolution of methane gas was seen from the homogeneous solution. To this mixture was added 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarboyl]-2-methoxycarbonylbenzenesulfonamide and the slurry was heated at reflux for 18 hours. The reaction mixture was then heated with aqueous hydrochloric acid and the precipitated product was purified by trituration in methylene chloride, 1.61 g, m.p. 172°-173° C. IR: 1700 cm⁻¹ unresolved carbonyls, NMR: in TFA 2.9 ppm s, CH₃ pyrimidine, 4.4ppm s, OCH₃ on pyrimidine, 5.4 ppm s, thiadiazole, 6.9 ppm s, proton in 5-position on pyrimidine, 8.1 and 8.5 ppm M, aromatic.

Using the procedures and examples described above and choosing the appropriate compounds of Formulae II and III (as illustrated in Table I), the compounds described in Tables II-VII may be prepared.

                  TABLE I                                                          ______________________________________                                         A: Structures                                                                  ______________________________________                                          ##STR17##                                                                                         ##STR18##                                                   ##STR19##                                                                                         ##STR20##                                                   ##STR21##                                                                                         ##STR22##                                                   ##STR23##                                                                                         ##STR24##                                                   ##STR25##                                                                                         ##STR26##                                                   ##STR27##                                                                                         ##STR28##                                                   ##STR29##                                                                                         ##STR30##                                                   ##STR31##                                                                                         ##STR32##                                                   ##STR33##                                                                                         ##STR34##                                                   ##STR35##                                                                                         ##STR36##                                                   ##STR37##                                                                                         ##STR38##                                                   ##STR39##                                                                                         ##STR40##                                                   ##STR41##                                                                                         ##STR42##                                                   ##STR43##                                                                                         ##STR44##                                                   ##STR45##                                                                                         ##STR46##                                                   ##STR47##                                                                                         ##STR48##                                                   ##STR49##                                                                                         ##STR50##                                                   ##STR51##                                                                                         ##STR52##                                                   ##STR53##                                                                                         ##STR54##                                                   ##STR55##                                                                                         ##STR56##                                                   ##STR57##                                                                                         ##STR58##                                                   ##STR59##                                                                                         ##STR60##                                                   ##STR61##                                                                                         ##STR62##                                                   ##STR63##                                                                                         ##STR64##                                                   ##STR65##                                                                                         ##STR66##                                                   ##STR67##                                                                                         ##STR68##                                                   ##STR69##                                                                                         ##STR70##                                                   ##STR71##                                                                                         ##STR72##                                                   ##STR73##                                                                                         ##STR74##                                                   ##STR75##                                                                                         ##STR76##                                                   ##STR77##                                                                                         ##STR78##                                                   ##STR79##                                                                                         ##STR80##                                                   ##STR81##                                                                                         ##STR82##                                                   ##STR83##                                                                                         ##STR84##                                                   ##STR85##                                                                                         ##STR86##                                                   ##STR87##                                                                                         ##STR88##                                                   ##STR89##                                                                                         ##STR90##                                                  ______________________________________                                    

                                      TABLE II                                     __________________________________________________________________________      ##STR91##                                                                     A  R  R.sub.1                                                                             R.sub.2                                                                           R.sub.3                                                                           R.sub.5                                                                              R.sub.6                                                                              X   Y     m.p.(°C.)                        __________________________________________________________________________     1  H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      1  H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                      2  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     2  H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                      3  H  H    H  H  2-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     3  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     4  H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     5  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     5  H  5-Cl H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     6  H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                                                             208-211                                 6  H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                                                            203-206                                 7  H  H    H  H  3-CH.sub.3                                                                           4-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                      8  H  5-F  H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     8  H  5-Br H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     9  H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      10 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     11 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     12 H  H    H  H  5-SCH.sub.3                                                                          --    CH.sub.3                                                                           CH.sub.3                                      12 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     12 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                                                             226-230                                 12 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                                                            180-182                                 13 H  H    H  H  3-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     14 H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      15 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      15 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                                                          OCH.sub.3                                     16 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     17 H  5-F  H  H  --    --    CH.sub.3                                                                           CH.sub.3                                      18 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                                                          CH.sub.3                                      19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                             149-151                                 19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                            173-175                                 20 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      21 H  5-OCH.sub.3                                                                         H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     22 H  5-CF.sub.3                                                                          H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      22 H  5-NO.sub.2                                                                          H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     23 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     24 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                      25 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      25 H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                     26 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      27 H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     28 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     29 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      29 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     29 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     30 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      31 H  5-Cl H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      31 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     31 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     32 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                                                             192-194                                 32 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                                                            185-187                                 32 H  H    H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                                                          OCH.sub.3                                     32 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     33 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      33 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     33 H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     34 H  H    H  H  2-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     34 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3 -34                                                                        H H H H H -- CH.sub.3 CH.sub.3          35 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                                                             168-170                                 35 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     35 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                                                            172-173                                 35 CH.sub.3                                                                          H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     35 H  H    CH.sub.3                                                                          H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     35 H  H    H  CH.sub.3                                                                          H     --    OCH.sub.3                                                                          OCH.sub.3                                     36 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      36 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     36 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     37 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      37 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     37 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     38 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     38 H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub. 3                                    39 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      39 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     40 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      40 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     41 H  H    H  H  4-Cl  --    CH.sub.3                                                                           CH.sub.3                                      41 H  H    H  H  4-CN  --    OCH.sub.3                                                                          CH.sub.3                                      41 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      41 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     41 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     42 H  H    H  H  4-Cl  --    CH.sub.3                                                                           OCH.sub.3                                     42 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     42 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      42 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     42 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     43 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                                                             215-216                                 43 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                                                            206-207                                 43 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     43 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     43 H  H    H  H  3-Cl  5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     43 H  H    H  H  3-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     43 H  H    H  H  4-N(CH.sub.3).sub.2                                                                  H     CH.sub.3                                                                           OCH.sub.3                                     43 H  H    H  H  5-CN  H     CH.sub.3                                                                           OCH.sub.3                                     44 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      44 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     44 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     45 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      45 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     45 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     46 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      46 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     46 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     46 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     46 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     47 H  H    H  H  H     H     CH.sub. 3                                                                          CH.sub.3                                      47 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     47 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     47 H  H    H  H  6-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     47 H  H    H  H  3-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     48 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     48 H  H    H  H  5-Cl  H     CH.sub.3                                                                           OCH.sub.3                                     48 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      48 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     48 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     49 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      49 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                             190-191                                 49 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                            184-185                                 49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                                                            198-199                                 49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                                                             188-190                                 49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                            202-204                                 49 H  H    H  H  4-Cl  6-Cl  CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-Cl  4-N(CH.sub.3).sub.2                                                                  CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-OCH.sub.3                                                                          6-SCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     49 H  H    H  H  4-Cl  6-CN  CH.sub.3                                                                           OCH.sub.3                                     50 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      50 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     50 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     50 H  H    H  H  2-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                     50 H  H    H  H  2-CH.sub.3                                                                           6-OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     50 H  H    H  H  2-CH.sub.3                                                                           6-Cl  CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      51 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     51 H  H    H  H  2-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                     51 H  H    H  H  OCH.sub.3                                                                            H     CH.sub.3                                                                           OCH.sub.3                                     52 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      52 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     52 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     52 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     52 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                     52 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                     53 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      53 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     53 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     53 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                     54 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      54 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     54 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     55 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      55 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     55 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     56 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      56 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     56 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     56 H  H    H  H  6-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     57 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     57 H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     58 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     58 H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     59 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                      59 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     59 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     59 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     59 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                     60 H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     61 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     61 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                     62 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     62 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     63 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     63 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     64 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     64 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     65 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     66 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     67 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     67 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     68 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     68 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     69 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     69 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     70 H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                     70 H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                     71 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      71 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub. 3                                    71 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                     71 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                     71 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                     72 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      72 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     72 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                     72 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                     72 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                     73 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                      73 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                     73 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                     73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                     73 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                     73 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                     74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                      74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                     74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                     32 H  H    H  H  H     H     Cl  OCH.sub.3                                     32 H  H    H  H  H     H     OCH.sub.3                                                                          C.sub.2 H.sub.5                               32 H  H    H  H  H     H     OCH.sub.3                                                                          OC.sub.2 H.sub.5                              32 H  H    H  H  H     H     OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                            35 H  H    H  H  H     --    Cl  CH.sub.3                                      35 H  H    H  H  H     --    CH.sub.3                                                                           C.sub.2 H.sub.5                               35 H  H    H  H  H     --    CH.sub.3                                                                           OC.sub.2 H.sub.5                              35 H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            35 H  H    H  H  H     --    CH.sub.3                                                                           H                                             32 H  H    H  H  H     --    Cl  NH.sub.2                                      32 H  H    H  H  H     --    Cl  NHCH.sub.3                                    35 H  H    H  H  H     --    Cl  N(CH.sub.3).sub.2                             __________________________________________________________________________

                                      TABLE III                                    __________________________________________________________________________      ##STR92##                                                                     A R  R.sub.1                                                                             R.sub.2                                                                           R.sub.3                                                                           R.sub.5                                                                              R.sub.6                                                                              X   Y     m.p. (°C.)                        __________________________________________________________________________     1 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       1 H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                       2 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      2 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                       3 H  H    H  H  2-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                      3 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      4 H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      5 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      5 H  5-Cl H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      6 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       6 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                                                            194-197                                  7 H  H    H  H  3-CH.sub.3                                                                           4-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                       8 H  5-F  H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      8 H  5-Br H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                      9 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       10                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      11                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      12                                                                               H  H    H  H  5-SCH.sub.3                                                                          --    CH.sub.3                                                                           CH.sub.3                                       12                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      12                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       12                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                                                            176-179                                  13                                                                               H  H    H  H  3-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                      14                                                                               H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                       15                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       15                                                                               H  H    H  H  CH.sub.3                                                                             --    OCH.sub. 3                                                                         OCH.sub.3                                      16                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      17                                                                               H  5-F  H  H  --    --    CH.sub.3                                                                           CH.sub.3                                       18                                                                               H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                                                          CH.sub.3                                       19                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                       19                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                                                            142-144                                  20                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       21                                                                               H  5-OCH.sub.3                                                                         H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      22                                                                               H  5-CF.sub.3                                                                          H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       22                                                                               H  5-NO.sub.2                                                                          H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      23                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      24                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                       25                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       25                                                                               H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                      26                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       27                                                                               H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      28                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      29                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       29                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      29                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      30                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       31                                                                               H  5-Cl H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       31                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      31                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      32                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       32                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      32                                                                               H  H    H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                                                          OCH.sub.3                                      32                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      33                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       33                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      33                                                                               H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                      34                                                                               H  H    H  H  2-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      34                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      34                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       35                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      35                                                                               CH.sub.3                                                                          H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      35                                                                               H  H    CH.sub.3                                                                          H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      35                                                                               H  H    H  CH.sub.3                                                                          H     --    OCH.sub.3                                                                          OCH.sub.3                                      36                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       36                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      36                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      37                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       37                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      37                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      38                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      38                                                                               H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                      39                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       39                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      40                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       40                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      41                                                                               H  H    H  H  4-Cl  --    CH.sub.3                                                                           CH.sub.3                                       41                                                                               H  H    H  H  4-CN  --    OCH.sub.3                                                                          CH.sub.3                                       41                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       41                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      41                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      42                                                                               H  H    H  H  4-Cl  --    CH.sub.3                                                                           OCH.sub.3                                      42                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      42                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       42                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      42                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      43                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       43                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                                                            161-163                                  43                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      43                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                      43                                                                               H  H    H  H  3-Cl  5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                      43                                                                               H  H    H  H  3-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                      43                                                                               H  H    H  H  4-N(CH.sub.3).sub.2                                                                  H     CH.sub.3                                                                           OCH.sub.3                                      43                                                                               H  H    H  H  5-CN  H     CH.sub.3                                                                           OCH.sub.3                                      44                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       44                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      44                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      45                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       45                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      45                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      46                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       46                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      46                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      46                                                                               H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                      46                                                                               H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                      47                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       47                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      47                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      47                                                                               H  H    H  H  6-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                      47                                                                               H  H    H  H  3-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                      48                                                                               H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                      48                                                                               H  H    H  H  5-Cl  H     CH.sub.3                                                                           OCH.sub.3                                      48                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       48                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      48                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      49                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       49                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      49                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                       49                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      49                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                            172-173                                  49                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                      49                                                                               H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       49                                                                               H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                            194-196                                  49                                                                               H  H    H  H  4-Cl  6-Cl  CH.sub.3                                                                           OCH.sub.3                                      49                                                                               H  H    H  H  4-Cl  4-N(CH.sub.3).sub.2                                                                  CH.sub.3                                                                           OCH.sub.3                                      49                                                                               H  H    H  H  4-OCH.sub.3                                                                          6-SCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      49                                                                               H  H    H  H  4-Cl  6-CN  CH.sub.3                                                                           OCH.sub.3                                      50                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       50                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      50                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      50                                                                               H  H    H  H  2-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                      50                                                                               H  H    H  H  2-CH.sub.3                                                                           6-OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      50                                                                               H  H    H  H  2-CH.sub.3                                                                           6-Cl  CH.sub.3                                                                           OCH.sub.3                                      51                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       51                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      51                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      51                                                                               H  H    H  H  2-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                      51                                                                               H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                      51                                                                               H  H    H  H  OCH.sub.3                                                                            H     CH.sub.3                                                                           OCH.sub.3                                      52                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       52                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      52                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      52                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                      52                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                      52                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                      53                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       53                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      53                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      53                                                                               H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                      54                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       54                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      54                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      55                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       55                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      55                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      56                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       56                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      56                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      56                                                                               H  H    H  H  6-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                      57                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      57                                                                               H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      58                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      58                                                                               H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      59                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       59                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      59                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      59                                                                               H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                      59                                                                               H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                      60                                                                               H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      61                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      61                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      62                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      62                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      63                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      63                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      64                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      64                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      65                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      66                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      67                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      67                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      68                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      68                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      69                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      69                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      70                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      70                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      71                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       71                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      71                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      71                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                       71                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                      71                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                      71                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                      71                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                      72                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       72                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      72                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      72                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                       72                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                      72                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                      72                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                      72                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                      73                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       73                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      73                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      73                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                       73                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                      73                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                      73                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                      73                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           OCH.sub.3                                      74                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                       74                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                      74                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                                                          OCH.sub.3                                      32                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          C.sub.2 H.sub.5                                32                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OC.sub.2 H.sub.5                               32                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                             35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           C.sub.2 H.sub.5                                35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OC.sub.2 H.sub.5                               35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.2 OCH.sub.3                             35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           H                                              __________________________________________________________________________

                                      TABLE IV                                     __________________________________________________________________________      ##STR93##                                                                     A R  R.sub.1                                                                             R.sub.2                                                                           R.sub.3                                                                           R.sub.5                                                                              R.sub.6                                                                              X   Y     m.p. (°C.)                        __________________________________________________________________________     1 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       1 H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                       2 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      2 H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                       3 H  H    H  H  2-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                      3 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      4 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       5 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      5 H  5-Cl H  H  H     H     CH.sub.3                                                                           H                                              6 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       6 H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      7 H  H    H  H  3-CH.sub.3                                                                           4-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                       8 H  5-F  H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       8 H  5-Br H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                      9 H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       10                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      11                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       12                                                                               H  H    H  H  5-SCH.sub.3                                                                          --    CH.sub.3                                                                           CH.sub.3                                       12                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           H                                              12                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       12                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      13                                                                               H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                                                           H                                              14                                                                               H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                       15                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       15                                                                               H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                      16                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      17                                                                               H  5-F  H  H  --    --    CH.sub.3                                                                           CH.sub.3                                       18                                                                               H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                                                          CH.sub.3                                       19                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                       19                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                      20                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       21                                                                               H  5-OCH.sub.3                                                                         H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      22                                                                               H  5-CF.sub.3                                                                          H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       22                                                                               H  5-NO.sub.2                                                                          H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      23                                                                               H  H    H  H  H     --    CH.sub.3                                                                           H                                              24                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                       25                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       25                                                                               H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                      26                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       27                                                                               H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                                                          CH.sub.3                                       28                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      29                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       29                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      29                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      30                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       31                                                                               H  5-Cl H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       31                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      31                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      32                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       32                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      32                                                                               H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                                                           H                                              32                                                                               H  H    H  H  H     H     CH.sub.3                                                                           H                                              33                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       33                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      33                                                                               H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                                                          OCH.sub.3                                      34                                                                               H  H    H  H  2-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      34                                                                               H  H    H  H  H     --    CH.sub.3                                                                           H                                              34                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       35                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      35                                                                               CH.sub.3                                                                          H    H  H  H     --    CH.sub.3                                                                           H                                              35                                                                               H  H    CH.sub.3                                                                          H  H     --    CH.sub.3                                                                           CH.sub.3                                       35                                                                               H  H    H  CH.sub.3                                                                          H     --    CH.sub.3                                                                           CH.sub.3                                       36                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       36                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      36                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      37                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       37                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      37                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      38                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      38                                                                               H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                                                           OCH.sub.3                                      39                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       39                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      40                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       40                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      41                                                                               H  H    H  H  4-Cl  --    CH.sub.3                                                                           CH.sub.3                                       41                                                                               H  H    H  H  4-CN  --    OCH.sub.3                                                                          CH.sub.3                                       41                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      41                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       41                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      41                                                                               H  H    H  H  H     --    CH.sub.3                                                                           H                                              42                                                                               H  H    H  H  4-Cl  --    CH.sub.3                                                                           OCH.sub.3                                      42                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           OCH.sub.3                                      42                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       42                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      42                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      43                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       43                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      43                                                                               H  H    H  H  H     H     CH.sub.3                                                                           H                                              43                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                       43                                                                               H  H    H  H  3-Cl  5-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                       43                                                                               H  H    H  H  3-CH.sub.3                                                                           5-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                       43                                                                               H  H    H  H  4-N(CH.sub.3).sub.2                                                                  H     CH.sub.3                                                                           CH.sub.3                                       43                                                                               H  H    H  H  5-CN  H     CH.sub.3                                                                           CH.sub.3                                       44                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       44                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      44                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      45                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       45                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      45                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      46                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       46                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      46                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      46                                                                               H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                       46                                                                               H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           H                                              47                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       47                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      47                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      47                                                                               H  H    H  H  6-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                      47                                                                               H  H    H  H  3-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           H                                              48                                                                               H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           CH.sub.3                                       48                                                                               H  H    H  H  5-Cl  H     CH.sub.3                                                                           OCH.sub.3                                      48                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       48                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      48                                                                               H  H    H  H  H     H     CH.sub.3                                                                           H                                              49                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       49                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      49                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                       49                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      49                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                      49                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           H                                              49                                                                               H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       49                                                                               H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                      49                                                                               H  H    H  H  4-Cl  6-Cl  CH.sub.3                                                                           H                                              49                                                                               H  H    H  H  4-Cl  4-N(CH.sub.3).sub. 2                                                                 CH.sub.3                                                                           H                                              49                                                                               H  H    H  H  4-OCH.sub.3                                                                          6-SCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       49                                                                               H  H    H  H  4-Cl  6-CN  CH.sub.3                                                                           CH.sub.3                                       50                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       50                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      50                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      50                                                                               H  H    H  H  2-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                       50                                                                               H  H    H  H  2-CH.sub.3                                                                           6-OCH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                       50                                                                               H  H    H  H  2-CH.sub.3                                                                           6-Cl  CH.sub.3                                                                           OCH.sub.3                                      51                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       51                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      51                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      51                                                                               H  H    H  H  2-CH.sub.3                                                                           H     CH.sub.3                                                                           OCH.sub.3                                      51                                                                               H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                                                           H                                              51                                                                               H  H    H  H  OCH.sub.3                                                                            H     CH.sub.3                                                                           OCH.sub.3                                      52                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       52                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      52                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      52                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H                                              52                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                       52                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                       53                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       53                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      53                                                                               H  H    H  H  H     H     CH.sub.3                                                                           H                                              53                                                                               H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                       54                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       54                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      54                                                                               H  H    H  H  H     H     CH.sub.3                                                                           H                                              55                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       55                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      55                                                                               H  H    H  H  H     H     CH.sub.3                                                                           H                                              56                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       56                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      56                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      56                                                                               H  H    H  H  6-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                       57                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      57                                                                               H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                       58                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      58                                                                               H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                       59                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       59                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      59                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      59                                                                               H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                       59                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           H                                              60                                                                               H  H    H  H  4-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                       61                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      61                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                                                           CH.sub.3                                       62                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      62                                                                               H  H    H  H  H     --    OCH.sub.3                                                                          OCH.sub.3                                      63                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      63                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       64                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      64                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       65                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      66                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       67                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      67                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       68                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      68                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       69                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      69                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       70                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OCH.sub.3                                      70                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.3                                       71                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       71                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      71                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      71                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                       71                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                      71                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H                                              71                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                       71                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                       72                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       72                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      72                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      72                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                       72                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                      72                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H                                              72                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                       72                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                       73                                                                               H  H    H  H  H     H     CH.sub.3                                                                           CH.sub.3                                       73                                                                               H  H    H  H  H     H     CH.sub.3                                                                           OCH.sub.3                                      73                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OCH.sub.3                                      73                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                       73                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                      73                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub. 3                                                                          H                                              73                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                       73                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                       74                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                       74                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           OCH.sub.3                                      74                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H                                              32                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          C.sub.2 H.sub.5                                32                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          OC.sub.2 H.sub.5                               32                                                                               H  H    H  H  H     H     OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                             35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           C.sub.2 H.sub.5                                35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           OC.sub.2 H.sub.5                               35                                                                               H  H    H  H  H     --    CH.sub.3                                                                           CH.sub.2 OCH.sub.3                             __________________________________________________________________________

                                      TABLE V                                      __________________________________________________________________________      ##STR94##                                                                     A R  R.sub.1                                                                             R.sub.2                                                                           R.sub.3                                                                           R.sub.5                                                                              R.sub.6                                                                              Y.sub.1                                                                            m.p. (°C.)                              __________________________________________________________________________      1                                                                               H  H    H  H  H     H     CH.sub.3                                            1                                                                               H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                            2                                                                               H  H    H  H  H     H     OCH.sub.3                                           2                                                                               H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                            3                                                                               H  H    H  H  2-CH.sub.3                                                                           5-CH.sub.3                                                                           OCH.sub.3                                           3                                                                               H  H    H  H  H     H     OCH.sub.3                                           4                                                                               H  H    H  H  H     H     OCH.sub.3                                           5                                                                               H  H    H  H  H     H     OCH.sub.3                                           5                                                                               H  5-Cl H  H  H     H     OCH.sub.3                                           6                                                                               H  H    H  H  H     H     CH.sub.3                                            6                                                                               H  H    H  H  H     H     OCH.sub.3                                           7                                                                               H  H    H  H  3-CH.sub.3                                                                           4-CH.sub.3                                                                           CH.sub.3                                            8                                                                               H  5-F  H  H  H     H     OCH.sub.3                                           8                                                                               H  5-Br H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                           9                                                                               H  H    H  H  H     H     CH.sub.3                                           10                                                                               H  H    H  H  H     H     OCH.sub.3                                          11                                                                               H  H    H  H  H     H     OCH.sub.3                                          12                                                                               H  H    H  H  5-SCH.sub.3                                                                          --    CH.sub.3                                           12                                                                               H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                          12                                                                               H  H    H  H  H     --    CH.sub.3                                           12                                                                               H  H    H  H  H     --    OCH.sub.3                                          13                                                                               H  H    H  H  3-CH.sub.3                                                                           --    OCH.sub.3                                          14                                                                               H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                           15                                                                               H  H    H  H  H     --    CH.sub.3                                           15                                                                               H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                          16                                                                               H  H    H  H  H     --    OCH.sub.3                                          17                                                                               H  5-F  H  H  --    --    CH.sub.3                                           18                                                                               H  H    H  H  CH.sub. 3                                                                            --    CH.sub.3                                           19                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                           19                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                          20                                                                               H  H    H  H  H     H     CH.sub.3                                           21                                                                               H  5-OCH.sub.3                                                                         H  H  H     H     OCH.sub.3                                          22                                                                               H  5-CF.sub.3                                                                          H  H  H     H     CH.sub.3                                           22                                                                               H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                          23                                                                               H  H    H  H  H     --    OCH.sub.3                                          24                                                                               H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                           25                                                                               H  H    H  H  H     --    CH.sub.3                                           25                                                                               H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                          26                                                                               H  H    H  H  H     --    CH.sub.3                                           27                                                                               H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                          28                                                                               H  H    H  H  H     --    OCH.sub.3                                          29                                                                               H  H    H  H  H     --    CH.sub.3                                           29                                                                               H  H    H  H  H     --    OCH.sub.3                                          30                                                                               H  H    H  H  H     --    CH.sub.3                                           31                                                                               H  5-Cl H  H  H     --    CH.sub.3                                           31                                                                               H  H    H  H  H     --    CH.sub.3                                           31                                                                               H  H    H  H  H     --    OCH.sub.3                                          32                                                                               H  H    H  H  H     H     CH.sub.3                                           32                                                                               H  H    H  H  H     H     OCH.sub.3                                          32                                                                               H  H    H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                          33                                                                               H  H    H  H  H     --    CH.sub.3                                           33                                                                               H  H    H  H  H     --    OCH.sub.3                                          33                                                                               H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                          34                                                                               H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                          34                                                                               H  H    H  H  H     --    OCH.sub.3                                          34                                                                               H  H    H  H  H     --    CH.sub.3                                           35                                                                               H  H    H  H  H     --    CH.sub.3                                           35                                                                               H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                          35                                                                               H  H    H  H  H     --    OCH.sub.3                                          35                                                                               CH.sub.3                                                                          H    H  H  H     --    OCH.sub.3                                          35                                                                               H  H    CH.sub.3                                                                          H  H     --    OCH.sub.3                                          35                                                                               H  H    H  CH.sub.3                                                                          H     --    OCH.sub.3                                          36                                                                               H  H    H  H  H     --    CH.sub.3                                           36                                                                               H  H    H  H  H     --    OCH.sub.3                                          37                                                                               H  H    H  H  H     --    CH.sub.3                                           37                                                                               H  H    H  H  H     --    OCH.sub.3                                          38                                                                               H  H    H  H  H     --    OCH.sub.3                                          38                                                                               H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                          39                                                                               H  H    H  H  H     --    CH.sub.3                                           39                                                                               H  H    H  H  H     --    OCH.sub.3                                          40                                                                               H  H    H  H  H     --    CH.sub.3                                           40                                                                               H  H    H  H  H     --    OCH.sub.3                                          41                                                                               H  H    H  H  4-Cl  --    CH.sub.3                                           41                                                                               H  H    H  H  4-CN  --    CH.sub.3                                           41                                                                               H  H    H  H  H     --    CH.sub.3                                           41                                                                               H  H    H  H  H     --    OCH.sub.3                                          42                                                                               H  H    H  H  4-Cl  --    OCH.sub.3                                          42                                                                               H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                          42                                                                               H  H    H  H  H     --    CH.sub.3                                           42                                                                               H  H    H  H  H     --    OCH.sub.3                                          43                                                                               H  H    H  H  H     H     CH.sub.3                                           43                                                                               H  H    H  H  H     H     OCH.sub.3                                          43                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                          43                                                                               H  H    H  H  3-Cl  5-CH.sub.3                                                                           OCH.sub.3                                          43                                                                               H  H    H  H  3-CH.sub.3                                                                           5-CH.sub.3                                                                           OCH.sub.3                                          43                                                                               H  H    H  H  4-N(CH.sub.3).sub.2                                                                  H     OCH.sub.3                                          43                                                                               H  H    H  H  5-CN  H     OCH.sub.3                                          44                                                                               H  H    H  H  H     H     CH.sub.3                                           44                                                                               H  H    H  H  H     H     OCH.sub.3                                          45                                                                               H  H    H  H  H     H     CH.sub.3                                           45                                                                               H  H    H  H  H     H     OCH.sub.3                                          46                                                                               H  H    H  H  H     H     CH.sub.3                                           46                                                                               H  H    H  H  H     H     OCH.sub.3                                          46                                                                               H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                          46                                                                               H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                          47                                                                               H  H    H  H  H     H     CH.sub.3                                           47                                                                               H  H    H  H  H     H     OCH.sub.3                                          47                                                                               H  H    H  H  6-CH.sub.3                                                                           H     OCH.sub.3                                          47                                                                               H  H    H  H  3-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                          48                                                                               H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                          48                                                                               H  H    H  H  5-Cl  H     OCH.sub.3                                          48                                                                               H  H    H  H  H     H     CH.sub.3                                           48                                                                               H  H    H  H  H     H     OCH.sub.3                                          49                                                                               H  H    H  H  H     H     CH.sub.3                                           49                                                                               H  H    H  H  H     H     OCH.sub.3                                          49                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                           49                                                                               H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                          49                                                                               H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                           49                                                                               H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          OCH.sub.3                                          49                                                                               H  H    H  H  4-Cl  6-Cl  OCH.sub.3                                          49                                                                               H  H    H  H  4-Cl  4-N(CH.sub.3).sub.2                                                                  OCH.sub.3                                          49                                                                               H  H    H  H  4-OCH.sub.3                                                                          6-SCH.sub.3                                                                          OCH.sub.3                                          49                                                                               H  H    H  H  4-Cl  6-CN  OCH.sub.3                                          50                                                                               H  H    H  H  H     H     CH.sub.3                                           50                                                                               H  H    H  H  H     H     OCH.sub.3                                          50                                                                               H  H    H  H  2-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                          50                                                                               H  H    H  H  2-CH.sub.3                                                                           6-OCH.sub.3                                                                          OCH.sub.3                                          50                                                                               H  H    H  H  2-CH.sub.3                                                                           6-Cl  OCH.sub.3                                          51                                                                               H  H    H  H  H     H     CH.sub.3                                           51                                                                               H  H    H  H  H     H     OCH.sub.3                                          51                                                                               H  H    H  H  2-CH.sub.3                                                                           H     OCH.sub.3                                          51                                                                               H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                          51                                                                               H  H    H  H  OCH.sub.3                                                                            H     OCH.sub.3                                          52                                                                               H  H    H  H  H     H     CH.sub.3                                           52                                                                               H  H    H  H  H     H     OCH.sub.3                                          52                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                          52                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                          52                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                          53                                                                               H  H    H  H  H     H     CH.sub.3                                           53                                                                               H  H    H  H  H     H     OCH.sub.3                                          53                                                                               H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                          54                                                                               H  H    H  H  H     H     CH.sub.3                                           54                                                                               H  H    H  H  H     H     OCH.sub.3                                          55                                                                               H  H    H  H  H     H     CH.sub.3                                           55                                                                               H  H    H  H  H     H     OCH.sub.3                                          56                                                                               H  H    H  H  H     --    CH.sub.3                                           56                                                                               H  H    H  H  H     --    OCH.sub.3                                          56                                                                               H  H    H  H  6-CH.sub.3                                                                           --    OCH.sub.3                                          57                                                                               H  H    H  H  H     --    OCH.sub.3                                          57                                                                               H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                          58                                                                               H  H    H  H  H     --    OCH.sub.3                                          58                                                                               H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                          59                                                                               H  H    H  H  H     --    CH.sub.3                                           59                                                                               H  H    H  H  H     --    OCH.sub.3                                          59                                                                               H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                          59                                                                               H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                          60                                                                               H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub. 3                                         61                                                                               H  H    H  H  H     --    OCH.sub.3                                          61                                                                               H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                          62                                                                               H  H    H  H  H     --    CH.sub.3                                           62                                                                               H  H    H  H  H     --    OCH.sub.3                                          63                                                                               H  H    H  H  H     --    CH.sub.3                                           63                                                                               H  H    H  H  H     --    OCH.sub.3                                          64                                                                               H  H    H  H  H     --    CH.sub.3                                           64                                                                               H  H    H  H  H     --    OCH.sub.3                                          65                                                                               H  H    H  H  H     --    OCH.sub.3                                          66                                                                               H  H    H  H  H     --    OCH.sub.3                                          67                                                                               H  H    H  H  H     --    CH.sub.3                                           67                                                                               H  H    H  H  H     --    OCH.sub.3                                          68                                                                               H  H    H  H  H     --    CH.sub.3                                           68                                                                               H  H    H  H  H     --    OCH.sub.3                                          69                                                                               H  H    H  H  H     --    CH.sub.3                                           69                                                                               H  H    H  H  H     --    OCH.sub.3                                          70                                                                               H  H    H  H  H     --    CH.sub.3                                           70                                                                               H  H    H  H  H     --    OCH.sub.3                                          71                                                                               H  H    H  H  H     H     CH.sub.3                                           71                                                                               H  H    H  H  H     H     OCH.sub.3                                          71                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                           71                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                          71                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                          71                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                          72                                                                               H  H    H  H  H     H     CH.sub.3                                           72                                                                               H  H    H  H  H     H     OCH.sub.3                                          72                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                           72                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                          72                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                          72                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                          73                                                                               H  H    H  H  H     H     CH.sub.3                                           73                                                                               H  H    H  H  H     H     OCH.sub.3                                          73                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                           73                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                          73                                                                               H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                          73                                                                               H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                          74                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                           74                                                                               H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                          32                                                                               H  H    H  H  H     H     Cl                                                 32                                                                               H  H    H  H  H     H     H                                                  35                                                                               H  H    H  H  H     --    Cl                                                 35                                                                               H  H    H  H  H     --    H                                                  __________________________________________________________________________

                                      TABLE VI                                     __________________________________________________________________________      ##STR95##                                                                     A  R  R.sub.1                                                                             R.sub.2                                                                           R.sub.3                                                                           R.sub.5                                                                              R.sub.6                                                                              Y.sub.1                                                                            m.p. (°C.)                             __________________________________________________________________________     1  H  H    H  H  H     H     CH.sub.3                                          1  H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                          2  H  H    H  H  H     H     OCH.sub.3                                         2  H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                          3  H  H    H  H  2-CH.sub.3                                                                           5-CH.sub.3                                                                           OCH.sub.3                                         3  H  H    H  H  H     H     OCH.sub.3                                         4  H  H    H  H  H     H     OCH.sub.3                                         5  H  H    H  H  H     H     OCH.sub.3                                         5  H  5-Cl H  H  H     H     OCH.sub.3                                         6  H  H    H  H  H     H     CH.sub.3                                          6  H  H    H  H  H     H     OCH.sub.3                                         7  H  H    H  H  3-CH.sub.3                                                                           4-CH.sub.3                                                                           CH.sub.3                                          8  H  5-F  H  H  H     H     OCH.sub.3                                         8  H  5-Br H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                         9  H  H    H  H  H     H     CH.sub.3                                          10 H  H    H  H  H     H     OCH.sub.3                                         11 H  H    H  H  H     H     OCH.sub.3                                         12 H  H    H  H  5-SCH.sub.3                                                                          --    CH.sub.3                                          12 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         12 H  H    H  H  H     --    CH.sub.3                                          12 H  H    H  H  H     --    OCH.sub.3                                         13 H  H    H  H  3-CH.sub.3                                                                           --    OCH.sub.3                                         14 H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                          15 H  H    H  H  H     --    CH.sub.3                                          15 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                         16 H  H    H  H  H     --    OCH.sub.3                                         17 H  5-F  H  H  --    --    CH.sub.3                                          18 H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                          19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         20 H  H    H  H  H     H     CH.sub.3                                          21 H  5-OCH.sub.3                                                                         H  H  H     H     OCH.sub.3                                         22 H  5-CF.sub.3                                                                          H  H  H     H     CH.sub.3                                          22 H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                         23 H  H    H  H  H     --    OCH.sub.3                                         24 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                          25 H  H    H  H  H     --    CH.sub.3                                          25 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                         26 H  H    H  H  H     --    CH.sub.3                                          27 H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                         28 H  H    H  H  H     --    OCH.sub.3                                         29 H  H    H  H  H     --    CH.sub.3                                          29 H  H    H  H  H     --    OCH.sub.3                                         30 H  H    H  H  H     --    CH.sub.3                                          31 H  5-Cl H  H  H     --    CH.sub.3                                          31 H  H    H  H  H     --    CH.sub.3                                          31 H  H    H  H  H     --    OCH.sub.3                                         32 H  H    H  H  H     H     CH.sub.3                                          32 H  H    H  H  H     H     OCH.sub.3                                         32 H  H    H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                         33 H  H    H  H  H     --    CH.sub.3                                          33 H  H    H  H  H     --    OCH.sub.3                                         33 H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                         34 H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                         34 H  H    H  H  H     --    OCH.sub.3                                         34 H  H    H  H  H     --    CH.sub.3                                          35 H  H    H  H  H     --    CH.sub.3                                          35 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         35 H  H    H  H  H     --    OCH.sub.3                                         35 CH.sub.3                                                                          H    H  H  H     --    OCH.sub.3                                         35 H  H    CH.sub.3                                                                          H  H     --    OCH.sub.3                                         35 H  H    H  CH.sub.3                                                                          H     --    OCH.sub.3                                         36 H  H    H  H  H     --    CH.sub.3                                          36 H  H    H  H  H     --    OCH.sub.3                                         37 H  H    H  H  H     --    CH.sub.3                                          37 H  H    H  H  H     --    OCH.sub.3                                         38 H  H    H  H  H     --    OCH.sub.3                                         38 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                         39 H  H    H  H  H     --    CH.sub.3                                          39 H  H    H  H  H     --    OCH.sub.3                                         40 H  H    H  H  H     --    CH.sub.3                                          40 H  H    H  H  H     --    OCH.sub.3                                         41 H  H    H  H  4-Cl  --    CH.sub.3                                          41 H  H    H  H  4-CN  --    CH.sub.3                                          41 H  H    H  H  H     --    CH.sub.3                                          41 H  H    H  H  H     --    OCH.sub.3                                         42 H  H    H  H  4-Cl  --    OCH.sub.3                                         42 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         42 H  H    H  H  H     --    CH.sub.3                                          42 H  H    H  H  H     --    OCH.sub.3                                         43 H  H    H  H  H     H     CH.sub.3                                          43 H  H    H  H  H     H     OCH.sub.3                                         43 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         43 H  H    H  H  3-Cl  5-CH.sub.3                                                                           OCH.sub.3                                         43 H  H    H  H  3-CH.sub.3                                                                           5-CH.sub.3                                                                           OCH.sub.3                                         43 H  H    H  H  4-N(CH.sub.3).sub.2                                                                  H     OCH.sub.3                                         43 H  H    H  H  5-CN  H     OCH.sub.3                                         44 H  H    H  H  H     H     CH.sub.3                                          44 H  H    H  H  H     H     OCH.sub.3                                         45 H  H    H  H  H     H     CH.sub.3                                          45 H  H    H  H  H     H     OCH.sub.3                                         46 H  H    H  H  H     H     CH.sub.3                                          46 H  H    H  H  H     H     OCH.sub.3                                         46 H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                         46 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         47 H  H    H  H  H     H     CH.sub.3                                          47 H  H    H  H  H     H     OCH.sub.3                                         47 H  H    H  H  6-CH.sub.3                                                                           H     OCH.sub.3                                         47 H  H    H  H  3-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         48 H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                         48 H  H    H  H  5-Cl  H     OCH.sub.3                                         48 H  H    H  H  H     H     CH.sub.3                                          48 H  H    H  H  H     H     OCH.sub.3                                         49 H  H    H  H  H     H     CH.sub.3                                          49 H  H    H  H  H     H     OCH.sub.3                                         49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                          49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                          49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          OCH.sub.3                                         49 H  H    H  H  4-Cl  6-Cl  OCH.sub.3                                         49 H  H    H  H  4-Cl  4-N(CH.sub.3).sub.2                                                                  OCH.sub.3                                         49 H  H    H  H  4-OCH.sub.3                                                                          6-SCH.sub.3                                                                          OCH.sub.3                                         49 H  H    H  H  4-Cl  6-CN  OCH.sub.3                                         50 H  H    H  H  H     H     CH.sub.3                                          50 H  H    H  H  H     H     OCH.sub.3                                         50 H  H    H  H  2-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         50 H  H    H  H  2-CH.sub.3                                                                           6-OCH.sub.3                                                                          OCH.sub.3                                         50 H  H    H  H  2-CH.sub.3                                                                           6-Cl  OCH.sub.3                                         51 H  H    H  H  H     H     CH.sub.3                                          51 H  H    H  H  H     H     OCH.sub.3                                         51 H  H    H  H  2-CH.sub.3                                                                           H     OCH.sub.3                                         51 H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                         51 H  H    H  H  OCH.sub.3                                                                            H     OCH.sub.3                                         52 H  H    H  H  H     H     CH.sub.3                                          52 H  H    H  H  H     H     OCH.sub.3                                         52 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         52 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         52 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         53 H  H    H  H  H     H     CH.sub.3                                          53 H  H    H  H  H     H     OCH.sub.3                                         53 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         54 H  H    H  H  H     H     CH.sub.3                                          54 H  H    H  H  H     H     OCH.sub.3                                         55 H  H    H  H  H     H     CH.sub.3                                          55 H  H    H  H  H     H     OCH.sub.3                                         56 H  H    H  H  H     --    CH.sub.3                                          56 H  H    H  H  H     --    OCH.sub.3                                         56 H  H    H  H  6-CH.sub.3                                                                           --    OCH.sub.3                                         57 H  H    H  H  H     --    OCH.sub.3                                         57 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         58 H  H    H  H  H     --    OCH.sub.3                                         58 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         59 H  H    H  H  H     --    CH.sub.3                                          59 H  H    H  H  H     --    OCH.sub.3                                         59 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         59 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         60 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         61 H  H    H  H  H     --    OCH.sub.3                                         61 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         62 H  H    H  H  H     --    CH.sub.3                                          62 H  H    H  H  H     --    OCH.sub.3                                         63 H  H    H  H  H     --    CH.sub.3                                          63 H  H    H  H  H     --    OCH.sub.3                                         64 H  H    H  H  H     --    CH.sub.3                                          64 H  H    H  H  H     --    OCH.sub.3                                         65 H  H    H  H  H     --    OCH.sub.3                                         66 H  H    H  H  H     --    OCH.sub.3                                         67 H  H    H  H  H     --    CH.sub.3                                          67 H  H    H  H  H     --    OCH.sub.3                                         68 H  H    H  H  H     --    CH.sub.3                                          68 H  H    H  H  H     --    OCH.sub.3                                         69 H  H    H  H  H     --    CH.sub.3                                          69 H  H    H  H  H     --    OCH.sub.3                                         70 H  H    H  H  H     --    CH.sub.3                                          70 H  H    H  H  H     --    OCH.sub.3                                         71 H  H    H  H  H     H     CH.sub.3                                          71 H  H    H  H  H     H     OCH.sub.3                                         71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         71 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         71 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         72 H  H    H  H  H     H     CH.sub.3                                          72 H  H    H  H  H     H     OCH.sub.3                                         72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         72 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         72 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         73 H  H    H  H  H     H     CH.sub.3                                          73 H  H    H  H  H     H     OCH.sub.3                                         73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         73 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         73 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         32 H  H    H  H  H     H     Cl                                                32 H  H    H  H  H     H     H                                                 35 H  H    H  H  H     --    Cl                                                35 H  H    H  H  H     --    H                                                 __________________________________________________________________________

                                      TABLE VII                                    __________________________________________________________________________      ##STR96##                                                                     A  R  R.sub.1                                                                             R.sub.2                                                                           R.sub.3                                                                           R.sub.5                                                                              R.sub.6                                                                              Y.sub.1                                                                            m.p. (°C.)                             __________________________________________________________________________     1  H  H    H  H  H     H     CH.sub.3                                          1  H  H    H  H  4-CH.sub.3                                                                           H     CH.sub.3                                          2  H  H    H  H  H     H     OCH.sub.3                                         2  H  H    H  H  5-CH.sub.3                                                                           H     CH.sub.3                                          3  H  H    H  H  2-CH.sub.3                                                                           5-CH.sub.3                                                                           OCH.sub.3                                         3  H  H    H  H  H     H     OCH.sub.3                                         4  H  H    H  H  H     H     OCH.sub.3                                         5  H  H    H  H  H     H     OCH.sub.3                                         5  H  5-Cl H  H  H     H     OCH.sub. 3                                        6  H  H    H  H  H     H     CH.sub.3                                          6  H  H    H  H  H     H     OCH.sub.3                                         7  H  H    H  H  3-CH.sub.3                                                                           4-CH.sub.3                                                                           CH.sub.3                                          8  H  5-F  H  H  H     H     OCH.sub.3                                         8  H  5-Br H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                         9  H  H    H  H  H     H     CH.sub.3                                          10 H  H    H  H  H     H     OCH.sub.3                                         11 H  H    H  H  H     H     OCH.sub.3                                         12 H  H    H  H  5-SCH.sub.3                                                                          --    CH.sub.3                                          12 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         12 H  H    H  H  H     --    CH.sub.3                                          12 H  H    H  H  H     --    OCH.sub.3                                         13 H  H    H  H  3-CH.sub.3                                                                           --    OCH.sub.3                                         14 H  H    H  H  3-CH.sub.3                                                                           --    CH.sub.3                                          15 H  H    H  H  H     --    CH.sub.3                                          15 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                         16 H  H    H  H  H     --    OCH.sub.3                                         17 H  5-F  H  H  --    --    CH.sub.3                                          18 H  H    H  H  CH.sub.3                                                                             --    CH.sub.3                                          19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          19 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         20 H  H    H  H  H     H     CH.sub.3                                          21 H  5-OCH.sub.3                                                                         H  H  H     H     OCH.sub.3                                         22 H  5-CF.sub.3                                                                          H  H  H     H     CH.sub.3                                          22 H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                         23 H  H    H  H  H     --    OCH.sub.3                                         24 H  H    H  H  5-CH.sub.3                                                                           --    CH.sub.3                                          25 H  H    H  H  H     --    CH.sub.3                                          25 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                         26 H  H    H  H  H     --    CH.sub.3                                          27 H  5-NO.sub.2                                                                          H  H  H     --    OCH.sub.3                                         28 H  H    H  H  H     --    OCH.sub.3                                         29 H  H    H  H  H     --    CH.sub.3                                          29 H  H    H  H  H     --    OCH.sub.3                                         30 H  H    H  H  H     --    CH.sub.3                                          31 H  5-Cl H  H  H     --    CH.sub.3                                          31 H  H    H  H  H     --    CH.sub.3                                          31 H  H    H  H  H     --    OCH.sub.3                                         32 H  H    H  H  H     H     CH.sub.3                                          32 H  H    H  H  H     H     OCH.sub.3                                         32 H  H    H  H  4-CH.sub.3                                                                           H     OCH.sub.3                                         33 H  H    H  H  H     --    CH.sub.3                                          33 H  H    H  H  H     --    OCH.sub.3                                         33 H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                         34 H  H    H  H  2-CH.sub.3                                                                           --    OCH.sub.3                                         34 H  H    H  H  H     --    OCH.sub.3                                         34 H  H    H  H  H     --    CH.sub.3                                          35 H  H    H  H  H     --    CH.sub.3                                          35 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         35 H  H    H  H  H     --    OCH.sub.3                                         35 CH.sub.3                                                                          H    H  H  H     --    OCH.sub.3                                         35 H  H    CH.sub.3                                                                          H  H     --    OCH.sub.3                                         35 H  H    H  CH.sub.3                                                                          H     --    OCH.sub.3                                         36 H  H    H  H  H     --    CH.sub.3                                          36 H  H    H  H  H     --    OCH.sub.3                                         37 H  H    H  H  H     --    CH.sub.3                                          37 H  H    H  H  H     --    OCH.sub.3                                         38 H  H    H  H  H     --    OCH.sub.3                                         38 H  H    H  H  CH.sub.3                                                                             --    OCH.sub.3                                         39 H  H    H  H  H     --    CH.sub.3                                          39 H  H    H  H  H     --    OCH.sub.3                                         40 H  H    H  H  H     --    CH.sub.3                                          40 H  H    H  H  H     --    OCH.sub.3                                         41 H  H    H  H  4-Cl  --    CH.sub.3                                          41 H  H    H  H  4-CN  --    CH.sub.3                                          41 H  H    H  H  H     --    CH.sub.3                                          41 H  H    H  H  H     --    OCH.sub.3                                         42 H  H    H  H  4-Cl  --    OCH.sub.3                                         42 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         42 H  H    H  H  H     --    CH.sub.3                                          42 H  H    H  H  H     --    OCH.sub.3                                         43 H  H    H  H  H     H     CH.sub.3                                          43 H  H    H  H  H     H     OCH.sub.3                                         43 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         43 H  H    H  H  3-Cl  5-CH.sub.3                                                                           OCH.sub.3                                         43 H  H    H  H  3-CH.sub.3                                                                           5-CH.sub.3                                                                           OCH.sub.3                                         43 H  H    H  H  4-N(CH.sub.3).sub.2                                                                  H     OCH.sub.3                                         43 H  H    H  H  5-CN  H     OCH.sub.3                                         44 H  H    H  H  H     H     CH.sub.3                                          44 H  H    H  H  H     H     OCH.sub.3                                         45 H  H    H  H  H     H     CH.sub.3                                          45 H  H    H  H  H     H     OCH.sub.3                                         46 H  H    H  H  H     H     CH.sub.3                                          46 H  H    H  H  H     H     OCH.sub.3                                         46 H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                         46 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         47 H  H    H  H  H     H     CH.sub.3                                          47 H  H    H  H  H     H     OCH.sub.3                                         47 H  H    H  H  6-CH.sub.3                                                                           H     OCH.sub.3                                         47 H  H    H  H  3-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         48 H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                         48 H  H    H  H  5-Cl  H     OCH.sub.3                                         48 H  H    H  H  H     H     CH.sub.3                                          48 H  H    H  H  H     H     OCH.sub.3                                         49 H  H    H  H  H     H     CH.sub.3                                          49 H  H    H  H  H     H     OCH.sub.3                                         49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           CH.sub.3                                          49 H  H    H  H  4-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          CH.sub.3                                          49 H  H    H  H  4-OCH.sub.3                                                                          6-OCH.sub.3                                                                          OCH.sub.3                                         49 H  H    H  H  4-Cl  6-Cl  OCH.sub.3                                         49 H  H    H  H  4-Cl  4-N(CH.sub.3).sub.2                                                                  OCH.sub.3                                         49 H  H    H  H  4-OCH.sub.3                                                                          6-SCH.sub.3                                                                          OCH.sub.3                                         49 H  H    H  H  4-Cl  6-CN  OCH.sub.3                                         50 H  H    H  H  H     H     CH.sub.3                                          50 H  H    H  H  H     H     OCH.sub.3                                         50 H  H    H  H  2-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         50 H  H    H  H  2-CH.sub.3                                                                           6-OCH.sub.3                                                                          OCH.sub.3                                         50 H  H    H  H  2-CH.sub.3                                                                           6-Cl  OCH.sub.3                                         51 H  H    H  H  H     H     CH.sub.3                                          51 H  H    H  H  H     H     OCH.sub.3                                         51 H  H    H  H  2-CH.sub.3                                                                           H     OCH.sub.3                                         51 H  H    H  H  5-CH.sub.3                                                                           H     OCH.sub.3                                         51 H  H    H  H  OCH.sub.3                                                                            H     OCH.sub.3                                         52 H  H    H  H  H     H     CH.sub.3                                          52 H  H    H  H  H     H     OCH.sub.3                                         52 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         52 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         52 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         53 H  H    H  H  H     H     CH.sub.3                                          53 H  H    H  H  H     H     OCH.sub.3                                         53 H  H    H  H  5-CH.sub.3                                                                           6-CH.sub.3                                                                           OCH.sub.3                                         54 H  H    H  H  H     H     CH.sub.3                                          54 H  H    H  H  H     H     OCH.sub.3                                         55 H  H    H  H  H     H     CH.sub.3                                          55 H  H    H  H  H     H     OCH.sub.3                                         56 H  H    H  H  H     --    CH.sub.3                                          56 H  H    H  H  H     --    OCH.sub.3                                         56 H  H    H  H  6-CH.sub.3                                                                           --    OCH.sub.3                                         57 H  H    H  H  H     --    OCH.sub.3                                         57 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         58 H  H    H  H  H     --    OCH.sub.3                                         58 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         59 H  H    H  H  H     --    CH.sub.3                                          59 H  H    H  H  H     --    OCH.sub.3                                         59 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         59 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         60 H  H    H  H  4-CH.sub.3                                                                           --    OCH.sub.3                                         61 H  H    H  H  H     --    OCH.sub.3                                         61 H  H    H  H  5-CH.sub.3                                                                           --    OCH.sub.3                                         62 H  H    H  H  H     --    CH.sub.3                                          62 H  H    H  H  H     --    OCH.sub.3                                         63 H  H    H  H  H     --    CH.sub.3                                          63 H  H    H  H  H     --    OCH.sub.3                                         64 H  H    H  H  H     --    CH.sub.3                                          64 H  H    H  H  H     --    OCH.sub.3                                         65 H  H    H  H  H     --    OCH.sub.3                                         66 H  H    H  H  H     --    OCH.sub.3                                         67 H  H    H  H  H     --    CH.sub.3                                          67 H  H    H  H  H     --    OCH.sub.3                                         68 H  H    H  H  H     --    CH.sub.3                                          68 H  H    H  H  H     --    OCH.sub.3                                         69 H  H    H  H  H     --    CH.sub.3                                          69 H  H    H  H  H     --    OCH.sub.3                                         70 H  H    H  H  H     --    CH.sub.3                                          70 H  H    H  H  H     --    OCH.sub.3                                         71 H  H    H  H  H     H     CH.sub.3                                          71 H  H    H  H  H     H     OCH.sub.3                                         71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          71 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         71 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         71 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         72 H  H    H  H  H     H     CH.sub.3                                          72 H  H    H  H  H     H     OCH.sub.3                                         72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          72 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         72 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         72 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         73 H  H    H  H  H     H     CH.sub.3                                          73 H  H    H  H  H     H     OCH.sub.3                                         73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          73 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         73 H  H    H  H  CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                         73 H  H    H  H  OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                         74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                          74 H  H    H  H  CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                         32 H  H    H  H  H     H     Cl                                                32 H  H    H  H  H     H     H                                                 35 H  H    H  H  H     --    Cl                                                35 H  H    H  H  H     --    H                                                 __________________________________________________________________________

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE VIII                                                       ______________________________________                                                     Active  Weight Percent*                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74      1-10                                        Oil Suspensions,                                                                              3-50     40-95      0-15                                        Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84      1-20                                        Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9   0-15                                        High Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                          * Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 6 Wettable Powder

    ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                          80%                                                 aminsulfonyl]-N--(4,6-dimethylpyrimidin-2-yl)-                                 benzamide                                                                      sodium alkylnaphthalenesulfonate                                                                          2%                                                  sodium ligninsulfonate     2%                                                  synthetic amorphous silica 3%                                                  kaolinite                  13%                                                 ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

EXAMPLE 7 Wettable Powder

    ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      50%                                                aminosulfonyl]-N--(thiazol-2-yl)benzamide                                      sodium alkylnaphthalenesulfonate                                                                           2%                                                 low viscosity methyl cellulose                                                                             2%                                                 diatomaceous earth          46%                                                ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 8 Granule

    ______________________________________                                         Wettable Powder of Example 7                                                                           5%                                                     attapulgite granules   95%                                                     (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                              ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 9 Extruded Pellet

    ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      25%                                                aminosulfonyl]-N--(2-pyridinyl)benzamide                                       anhydrous sodium sulfate    10%                                                crude calcium ligninsulfonate                                                                               5%                                                sodium alkylnaphthalenesulfonate                                                                            1%                                                calcium/magnesium bentonite 59%                                                ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 10 Oil Suspension

    ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocar-                                                           25%                                                 bonyl]aminosulfonyl]-N--(1,3,4-thiadiazol-2-yl)-                               benzamide                                                                      polyoxyethylene sorbitol hexaoleate                                                                        5%                                                 highly aliphatic hydrocarbon oil                                                                          70%                                                 ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 11 Wettable Powder

    ______________________________________                                         N--(3,4-dimethylisoxazol-5-yl)-2-[[(4-methoxy-6-methyl-                                                   20%                                                 pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-                                   benzamide                                                                      sodium alkylnaphthalenesulfonate                                                                          4%                                                  sodium ligninsulfonate     4%                                                  low viscosity methyl cellulose                                                                            3%                                                  attapulgite                69%                                                 ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 12 Low Strength Granule

    ______________________________________                                         2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-                                                        1%                                                   carbonyl]aminosulfonyl]-N--(1-methyl-1H--pyrazol-                              3-yl)benzamide                                                                 N,N--dimethylformamide    9%                                                   attapulgite granules      90%                                                  (U.S.S. 20-40 sieve)                                                           ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 13 Aqueous Suspension

    ______________________________________                                         N--(3,4-dimethylisoxazol-5-yl)-2-[[(4-methoxy-6-methyl-                                                    40%                                                pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-                                   benzamide                                                                      polyacrylic acid thickener  0.3%                                               dodecylphenol polyethylene glycol ether                                                                    0.5%                                               disodium phosphate          1%                                                 monosodium phosphate        0.5%                                               polyvinyl alcohol           1.0%                                               water                       56.7%                                              ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 14 Solution

    ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                           5%                                                 aminosulfonyl]-N--(1,2,4-triazol-3-yl)-                                        benzamide, sodium salt                                                         water                      95%                                                 ______________________________________                                    

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 15 Low Strength Granule

    ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      0.1%                                               aminosulfonyl]-N--(thiazol-2-yl)benzamide                                                                  99.9%                                              attapulgite granules                                                           (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 16 Granule

    ______________________________________                                         2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-                                                          80%                                                carbonyl]aminosulfonyl]-N--1-methyl-1H--pyrazol-                               3-yl)benzamide                                                                 wetting agent                1%                                                crude ligninsulfonate salt (containing                                                                     10%                                                5-20% of the natural sugars)                                                   attapulgite clay             9%                                                ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 17 High Strength Concentrate

    ______________________________________                                         2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-                                                           99%                                                 aminosulfonyl]-N--(1,2,4-triazol-3-yl)-                                        benzamide                                                                      silica aerogel             0.5%                                                synthetic amorphous silica 0.5%                                                ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 18 Wettable Powder

    ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                      90%                                                aminosulfonyl]-N--(2-pyridinyl)benzamide                                       dioctyl sodium sulfosuccinate                                                                              0.1%                                               synthetic fine silica       9.9%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 19 Wettable Powder

    ______________________________________                                         2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocar-                                                           40%                                                 bonyl]aminosulfonyl]-N--(1,3,4-thiadiazol-2-yl)-                               benzamide                                                                      sodium ligninsulfonate     20%                                                 montmorillonite clay       40%                                                 ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 20 Oil Suspension

    ______________________________________                                         2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                          35%                                                 aminosulfonyl]-N--(4,6-dimethylpyrimidin-2-yl)-                                benzamide                                                                      blend of polyalcohol carboxylic                                                                            6%                                                 esters and oil soluble petroleum                                               sulfonates                                                                     xylene                     59%                                                 ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

Utility

The compounds of the present invention are powerful herbicides. They have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds are useful for the selective control of weeds in crops such as wheat and alfalfa.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.125 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, or for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any other commercial herbicide examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.

The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

Test A

Seeds of crabgrass (Digitaria sp. ), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with the chemicals dissolved in a non-phytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliolate leaf expanding, crabgrass, barnyardgrass and wild oats with two leaves, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three to five leaves were sprayed. Treated plants and controls were maintained in a greenhouse for sixteen days, whereupon all species were compared to controls and visually rated for response to treatment.

The ratings are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:

C=chlorosis/necrosis;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

I=increased chlorophyl;

S=albinism;

U=unusual pigmentation;

X=axillary stimulation; and

6Y=abscised buds or flowers.

The ratings for the compounds tested by this procedure are presented in Table A.

Some of the compounds included in this table, e.g. compounds 1, 3, 4 and 6, were relatively inactive at the very low rates of applications selected, i.e. 0.05 kg/ha. It can reasonably be expected that they would have performed better at higher treatment levels.

                  TABLE A                                                          ______________________________________                                         Structures                                                                      ##STR97##                Compound 1                                            ##STR98##                Compound 2                                            ##STR99##                Compound 3                                            ##STR100##               Compound 4                                            ##STR101##               Compound 5                                            ##STR102##               Compound 6                                            ##STR103##               Compound 7                                            ##STR104##               Compound 8                                            ##STR105##               Compound 9                                            ##STR106##               Compound 10                                           ##STR107##               Compound 11                                           ##STR108##               Compound 12                                           ##STR109##               Compound 13                                           ##STR110##               Compound 14                                           ##STR111##               Compound 15                                           ##STR112##               Compound 16                                           ##STR113##               Compound 17                                           ##STR114##               Compound 18                                           ##STR115##               Compound 19                                           ##STR116##               Compound 20                                           ##STR117##               Compound 21                                           ##STR118##               Compound 22                                           ##STR119##               Compound 23                                                    Cmpd. 1   Cmpd. 2   Cmpd. 3 Cmpd. 4                                  Rate kg/ha                                                                               0.05      0.05      0.05    0.05                                     ______________________________________                                         POST-                                                                          EMERGENCE                                                                      Bush bean 2G        4C,9G,6Y  0       0                                        Cotton    1H        2C,6G     0       2H                                       Morningglory                                                                             2H        4C,7G     3G      1H                                       Cocklebur 1H        3C,6G     0       1H                                       Cassia    0         2C        0       0                                        Nutsedge  0         0         0       0                                        Crabgrass 0         0         0       0                                        Barnyardgrass                                                                            0         5G        0       0                                        Wild Oats 0         0         0       0                                        Wheat     0         0         0       0                                        Corn      0         0         0       0                                        Soybean   2C,5G     1H,2C,6G  1H      0                                        Rice      0         2C        0       0                                        Sorghum   0         2C        0       0                                        PRE-                                                                           EMERGENCE                                                                      Morningglory                                                                             0         3C,5H     0       1C                                       Cocklebur 0         2C        0       0                                        Cassia    0         2C        0       0                                        Nutsedge  0         0         0       0                                        Crabgrass 0         2G        0       0                                        Barnyardgrass                                                                            0         1C        0       0                                        Wild Oats 0         3G        0       0                                        Wheat     0         2G        0       0                                        Corn      0         2C        0       1C                                       Soybean   0         2C        0       0                                        Rice      0         2C        0       0                                        Sorghum   0         2C,5G     0       0                                        ______________________________________                                                   Cmpd. 5   Cmpd. 6   Cmpd. 7 Cmpd. 8                                  Rate kg/ha                                                                               0.05      0.05      0.05    0.05                                     ______________________________________                                         POST-                                                                          EMERGENCE                                                                      Bush bean 6C,9G,6Y  0         9C      9C                                       Cotton    4C,9G     0         5C,9G   4C,9G                                    Morningglory                                                                             2C,8G     0         2C,5G   2C,9H                                    Cocklebur 2H,4G     0         2C,9G   1C,9H                                    Cassia    2C,5G     0         5C,9G   5C,9G                                    Nutsedge  1C,9G     0         9G      2C,9G                                    Crabgrass 1C,5G     0         2C,9G   2C,8G                                    Barnyardgrass                                                                            9H        0         5C,9G   5C,9H                                    Wild Oats 6G,5X     0         9G      2C,9G                                    Wheat     6G        0         2C,9G   1C,9G                                    Corn      3U,9H     0         5U,9G   2U,9H                                    Soybean   4C,9G     0         9C      9C                                       Rice      4C,9G     0         5C,9G   5C,9G                                    Sorghum   2C,9G     0         3C,9G   2C,9G                                    PRE-                                                                           EMERGENCE                                                                      Morningglory                                                                             8G        0         9G      9H                                       Cocklebur 9H        0         9G      9H                                       Cassia    5G        0         7G      8G                                       Nutsedge  10E       0         10E     9G                                       Crabgrass 3C        0         5G      5G                                       Barnyardgrass                                                                            2C,9H     0         2C,9H   3C,9H                                    Wild Oats 2C,7G     0         2C,8G   2C,8G                                    Wheat     1C,8G     0         9H      1C,9G                                    Corn      3C,8G     0         3C,9G   3C,9G                                    Soybean   1C,5H     0         7H      2C,7H                                    Rice      9H        0         10E     10E                                      Sorghum   1C,8G     0         5C,9H   2U,9G                                    ______________________________________                                                   Cmpd. 9   Cmpd. 10  Cmpd. 11                                                                               Cmpd. 12                                 Rate kg/ha                                                                               0.05      0.05      0.05    0.05                                     ______________________________________                                         POST-                                                                          EMERGENCE                                                                      Bush bean 0         6C,9G,6Y  5C,9G,6Y                                                                               4S,8G,                                                                         6Y                                       Cotton    0         5C,9G     1U,4C,9G                                                                               2C,7G                                    Morningglory                                                                             0         5C,9G     1C,3G   1C,6G                                    Cocklebur 0         1H        2C,8G   0                                        Cassia    0         2C        1C,5G   2C                                       Nutsedge  4G        1C        5C,9G   0                                        Crabgrass 1C,5G     0         2C,8G   0                                        Barnyardgrass                                                                            1C,5G     0         6C,9H   0                                        Wild Oats 0         0         1C,8G   0                                        Wheat     0         0         5C,9G   0                                        Corn      1C,4G     2C,6H     5U,9G   0                                        Soybean   1H        2C,7G     3C,9G   1C,1H                                    Rice      1C,5G     0         9C      0                                        Sorghum   1C,9G     1C,8H     9C      0                                        PRE-                                                                           EMERGENCE                                                                      Moringglory                                                                              0         9G        9G      4G                                       Cocklebur 9H        9H        9H      5H                                       Cassia    1C        1C        1C,5G   0                                        Nutsedge  2G        0         8G      0                                        Crabgrass 0         0         1C,5G   0                                        Barnyardgrass                                                                            2G        1C        1C,9H   0                                        Wild Oats 2G        0         1C,8G   0                                        Wheat     2G        0         9G      0                                        Corn      1C,6G     1C,6G     1U,9G   1C                                       Soybean   0         1C,2H     2C,6H   1H                                       Rice      1C,3G     1C,3G     9H      0                                        Sorghum   1C,5H     1C,5G     1C,9G   0                                        ______________________________________                                                   Cmpd. 13  Cmpd. 14  Cmpd. 15                                         Rate kg/ha                                                                               0.05      0.4       0.05                                             ______________________________________                                         POST-                                                                          EMERGENCE                                                                      Bush bean 9C        8D,9G,6Y  9C                                               Cotton    4C,9G     9G        2U,3C,                                                                         9G                                               Morningglory                                                                             2C,5G     --        10C                                              Cocklebur 4C,9G     4G        2C,8G                                            Cassia    6G        9G        6C,9G                                            Nutsedge  9G        9G        2C,4G                                            Crabgrass 2C,8G     5G        2C                                               Barnyardgrass                                                                            3C,9H     --        2C                                               Wild Oats 2C,9G     --        1C                                               Wheat     2C,9G     9G        1C                                               Corn      5U,9G     9C        3C,9H                                            Soybean   6C,9G     9G        9C                                               Rice      6C,9G     9G        2C,7G                                            Sorghum   2U,9G     9C        3C,8H                                            PRE-                                                                           EMERGENCE                                                                      Morningglory                                                                             9G        9G        9G                                               Cocklebur 9H        --        9H                                               Cassia    6G        9G        3C,9G                                            Nutsedge  10E       10E       10E                                              Crabgrass 2C,8G     2C,8G     3G                                               Barnyardgrass                                                                            2C,9H     3C,9G     2C,4G                                            Wild Oats 1C,9G     1C,8G     1C                                               Wheat     9G        1C,9G     0                                                Corn      2C,9G     1U,9G     2C,6G                                            Soybean   6H        9H        2C,4H                                            Rice      10E       10E       2C,5H                                            Sorghum   5C,9H     9H        2C,7G                                            ______________________________________                                                   Cmpd. 16  Cmpd. 17  Cmpd. 18                                                                               Cmpd. 19                                 Rate kg/ha                                                                               0.05      0.05      0.05    0.05                                     ______________________________________                                         POST-                                                                          EMERGENCE                                                                      Bush bean 5C,9G,6Y  9C        10D,9G  9D,9G,                                                                         6Y                                       Cotton    3C,9G     4C,8G     2U,5C,9G                                                                               2C,3H,                                                                         9G                                       Morningglory                                                                             5G        2C,8G     2C      1C,4G                                    Cocklebur 6G        4G        5C,9G   2G                                       Cassia    4G        2G        5C,8G   2C,4G                                    Nutsedge  2C,9G     8G        9G      7G                                       Crabgrass 1C,9G     5G        1C,9G   5G                                       Barnyardgrass                                                                            2C,9H     3C,9H     2C,9H   5C,9H                                    Wild Oats 9G        1C,5G     1C,9H   5G                                       Wheat     9G        1C,5G     9G      6G                                       Corn      1C,9G     2C,9H     3U,9G   2C,9H                                    Soybean   2C,7H     2C,9G     5C,9G   2C,8G                                    Rice      9G,5I     2C,9G     4C,9G   1C,9G                                    Sorghum   9G,5I     1C,9G     5U,9G   9G                                       PRE-                                                                           EMERGENCE                                                                      Morningglory                                                                             9G        9G        9G      9G                                       Cocklebur 9H        9H        9H      9H                                       Cassia    7G        8G        8G      8G                                       Nutsedge  10E       10E       10E     9G                                       Crabgrass 3C,7G     1C,5G     1C,5G   2C,4G                                    Barnyardgrass                                                                            2C,9G     5C,9H     3C,9H   9C                                       Wild Oats 9G        1C,9G     2C,9G   2C,9G                                    Wheat     9G        9G        9G      1C,9G                                    Corn      3C,9G     2C,9G     9G      1C,9G                                    Soybean   7H        8H        9H      1C,5G                                    Rice      10E       10E       10E     10E                                      Sorghum   5C,9H     2U,9G     6C,9H   2U,9G                                    ______________________________________                                                   Cmpd. 20  Cmpd. 21  Cmpd. 22                                                                               Cmpd. 23                                 Rate kg/ha                                                                               0.05      0.05      0.05    0.05                                     ______________________________________                                         POST-                                                                          EMERGENCE                                                                      Bush bean 9C        6C,9G     9C      7C,9G                                    Cotton    2U,5C,9G  6C,9G     6C,9G   4C,9G                                    Morningglory                                                                             2C,8G     2C        9C      3C,5G                                    Cocklebur 2G        4C,9G     5C,9G   1C,4G                                    Cassia    4C,6G     1C,3G     5C,9G   2C                                       Nutsedge  0         5C,9G     8G      2C,8G                                    Crabgrass 0         3C,9G     2C,8G   2C,8G                                    Barnyardgrass                                                                            0         9C        10C     3C,9H                                    Wild Oats 0         9G        9G      4C,9G                                    Wheat     0         4C,9G     5C,6G   2C,8G                                    Corn      1C,5H     5U,9G     5U,9C   2C,9H                                    Soybean   2C,9G     6C,9G     9C      6C,9G                                    Rice      4G        2C,9G     5C,9G   2C,9G                                    Sorghum   2C,9G     5C,9G     9C      2C,9G                                    PRE-                                                                           EMERGENCE                                                                      Morningglory                                                                             9G        9G        9G      9G                                       Cocklebur 7H        9H        9H      8H                                       Cassia    7G        8G        9G      7G                                       Nutsedge  0         10E       10E     10E                                      Crabgrass 1C        1C,7G     2C,8G   5G,1C                                    Barnyardgrass                                                                            1C        4C,9H     5C,9H   2C,9G                                    Wild Oats 0         2C,8G     2C,9H   2C,8G                                    Wheat     0         1C,9H     2C,9H   2C,9G                                    Corn      1C,4G     10E       9G      8G                                       Soybean   1C,3G     5H        9H      2C,6H                                    Rice      2C,4G     10E       10E     4C,9H                                    Sorghum   2C        5C,9H     5C,9H   9G                                       ______________________________________                                    

Test B

Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grassy weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention.

Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. The data are summarized in Table B. Note that certain compounds have relative tolerance for wheat.

                                      TABLE B                                      __________________________________________________________________________     PRE-EMERGENCE ON                                                               FALLSINGTON SILT LOAM                                                          __________________________________________________________________________             Compound 5                                                                             Compound 7                                                                             Compound 8                                                                             Compound 11                                                                            Compound 13                                                                            Compound                                                                               Compound 17            Rate kg/ha                                                                             .060                                                                               .250                                                                               .030                                                                               .120                                                                               .030                                                                               .120                                                                               .060                                                                               .250                                                                               .030                                                                               .120                                                                               0.25                                                                               0.0625                                                                             0.250.0625             __________________________________________________________________________     Crabgrass                                                                              0   0   0   4G,2H                                                                              0   4G  0   6G  0   3G  8G,3H                                                                              7G,3H                                                                              6G,3H 5G,2H            Barnyardgrass                                                                          4C,6G                                                                              5C,7G                                                                              5G,3H                                                                              7G,5H                                                                              6G,2H                                                                              8G,6C                                                                              7G,5H                                                                              9G,9C                                                                              3G  5G  8G,9C                                                                              8G,8C                                                                              8G,8C7G,5C             Sorghum 7G,5H                                                                              8G,5H                                                                              8G,5H                                                                              10C 6G,3H                                                                              8G  8G,8C                                                                              10C 5G,3H                                                                              9G,9C                                                                              10E 10C 9C,9G7G,5H             Wild Oats                                                                              5G  6G,3H                                                                              5G  7G  5G  7G  7G,3H                                                                              7G,6C                                                                              4G  6G,3H                                                                              6G,3C                                                                              6G,3H                                                                              6G,3H 5G               Johnsongrass                                                                           3G  7G,3H                                                                              7G,5H                                                                              7G,5H                                                                              4G,3H                                                                              7G,5H                                                                              6G,3H                                                                              7G,5H                                                                              4G  7G,5H                                                                              8G,5H                                                                              5H,7G                                                                              7G,5H 3H,4G            Dallisgrass                                                                            0   4G  2G  5G  0   4G  6G  8G,3H                                                                              2G  6G  7C,8G                                                                              8G,3H                                                                              6G5G                   Giant foxtail                                                                          0   7G,5H                                                                              2G  5G,3H                                                                              4G,3H                                                                              7G,3H                                                                              7G,5H                                                                              9G,5H                                                                              0   3G,2H                                                                              8G,9C                                                                              7G,5C                                                                              7G,6C6G,3C             Ky. bluegrass                                                                          5G,3H                                                                              6G,3H                                                                              6G,3H                                                                              6G,3H                                                                              5G  6G,3H                                                                              7G,7C                                                                              8G,8C                                                                              6G  7G  8G,8C                                                                              8G,7C                                                                              8G,8C7G                Cheatgrass                                                                             8G,8C                                                                              10C 7G  7G  6G  7G,5E                                                                              8G,9C                                                                              10E 8G  8G  10C 10C 7G,8C10C               Sugarbeets                                                                             7G,8C                                                                              9G,9C                                                                              8G,8C                                                                              9G,9C                                                                              8G,7C                                                                              9G,9C                                                                              7G,8C                                                                              9G,9C                                                                              6G,4C                                                                              8G,8C                                                                              8G,9C                                                                              8G,8C                                                                              8G,8C8G,8C             Corn    0   8G,5H                                                                              7G,5H                                                                              10C 3G  6G,3H                                                                              3H  7G,5H                                                                              3G  3G  9G,9C                                                                              9G,9C                                                                              5G,5H 3G               Mustard 10C 10C 8G,6C                                                                              9G,9C                                                                              8G,8C                                                                              9G,9C                                                                              9G,8C                                                                              10C 7G,6C                                                                              9G,9C                                                                              10C 8G,8C                                                                              9G,9C8G,8C             Cocklebur                                                                              5G  5G,3H                                                                              6G  7G,5H                                                                              3G  7G  3G  6G,3H                                                                              6G,5C                                                                              6G,2C                                                                              7G  5G  6G3G                   Pigweed 6G,5C                                                                              8G,8C                                                                              --  --  --  --  9G,9C                                                                              10C --  --  10C 10C 9G,9C10C               Nutsedge                                                                               9G  8G  10E 10E 0   10E 3G  10E 9G  10E 10E 8G  3G3G                   Cotton  8G,5C                                                                              7G  8G,8C                                                                              9G,9C                                                                              0   8G,8C                                                                              2G  9G,8C                                                                              7G,3H                                                                              8G,5H                                                                              9G  7G  7G6G                   Morningglory                                                                           7G  8G  5G  7G  0   8G  5G  8G,5C                                                                              7G  8G  9G,5C                                                                              7G,3C                                                                              9G,8C5G                Cassia  8G,3C                                                                              7G,3C                                                                              5G  5G  0   7G  4G,3C                                                                              7G,3C                                                                              5G  7G,5C                                                                              6G  3G  7G5G                   Teaweed 4G  4G  0   5C,7G                                                                              0   7G,3C                                                                              4G  6G  4G  7G,4C                                                                              6G,3C                                                                              3G  5G0                    Velvetleaf                                                                             6G,3H                                                                              7G,6C                                                                              8G,5H                                                                              9G,9C                                                                              6G,5H                                                                              10C 8G,5H                                                                              8G,7C                                                                              6G,3H                                                                              7G,5H                                                                              9G,5H                                                                              8G,5H                                                                              6G,3H 5G,3H            Jimsonweed                                                                             4G,4C                                                                              7G,6C                                                                              0   5G,3C                                                                              0   5G,5C                                                                              5G,3C                                                                              7G,5C                                                                              0   3G,3C                                                                              6G,3C                                                                              4G  6G,4C3G,4C             Soybean 4G,3H                                                                              6G,3H                                                                              4G  7G,5H                                                                              4G  8G,8C                                                                              3G,2C                                                                              9G,8C                                                                              3G,3H                                                                              5G,3H                                                                              7G,5H                                                                              4G,1C                                                                              5H,7G 5G,2H            Rice    7G,5H                                                                              10C 10E 10E 7G  10E 8G,8C                                                                              10C 9G,9C                                                                              10C 10E 10E 7G,5H 7G,5H            Wheat   4G  5G  4G  7G,3H                                                                              3G  6G,3H                                                                              4G  7G,5C                                                                              3G  4G  7G,3C                                                                              6G,2C                                                                              5G4G                   __________________________________________________________________________             Compound 18                                                                            Compound 19                                                                            Compound 20                                                                            Compound 21                                                                            Compound 22                                                                            Compound                                                                               Compound 14            Rate kg/ha                                                                             0.12                                                                               0.0312                                                                             0.12                                                                               0.0312                                                                             0.12                                                                               0.0312                                                                             0.12                                                                               0.0312                                                                             0.12                                                                               0.0312                                                                             0.12                                                                               0.0312                                                                             0.250.06               __________________________________________________________________________     Crabgrass                                                                              6G  5G  3G  0   0   0   7G  4G  5G  3G  0   0   3H0                    Barnyardgrass                                                                          8G,8C                                                                              8G,3C                                                                              7G,5C                                                                              5G,2C                                                                              0   0   8G  5G  8G,3H                                                                              6G,2H                                                                              5G  0   5G,3H 0                Sorghum 10C 9G,9C                                                                              7G,3H                                                                              6G,3H                                                                              3G  0   10C 7G,3H                                                                              9G,9C                                                                              9G,3H                                                                              7G,5H                                                                              2G  8G,5H 5G,5H            Wild Oats                                                                              6G,6C                                                                              6G,3C                                                                              6G,2H                                                                              4G  0   0   7G  4G  7G,3H                                                                              4G  4G  0   4G0                    Johnsongrass                                                                           8G,8C                                                                              8C,8G                                                                              7G,5H                                                                              4G,3H                                                                              0   0   7G  3G  8G  7G  3G  0   6G,3H 0                Dallisgrass                                                                            3H,8G                                                                              7G,3H                                                                              4G  3G  0   0   5G  0   5G  2G  3G  0   00                     Giant foxtail                                                                          8G,5H                                                                              8G,5H                                                                              6G,3H                                                                              4G  0   0   5G,3H                                                                              0   8G,5H                                                                              4G  3G  0   00                     Ky. bluegrass                                                                          7G,8C                                                                              7G,8C                                                                              6G  5G  3G  0   6G  5G  6C,6G                                                                              5G  5G  0   8G,8C5G,5H             Cheatgrass                                                                             10E 10E 7G,8C                                                                              6G  0   0   9G,9C                                                                              7G  10E 5G  0   0   3G,3H 3G               Sugarbeets                                                                             9G,9C                                                                              7G,7C                                                                              8G,8C                                                                              6G,5C                                                                              8G,8C                                                                              8G,8C                                                                              7G,7C                                                                              6G,5H                                                                              8G,8C                                                                              6G,3H                                                                              7G,6C                                                                              4G  7G,8C6G,7C             Corn    10E 10E 8C,8G                                                                              4G  2G  0   6G,5H                                                                              0   4G  0   0   0   3G,0                   Mustard 10C 8G,5C                                                                              9G,8C                                                                              5C,8G                                                                              7G,5C                                                                              5G  9G,9C                                                                              8G,8C                                                                              9G,9C                                                                              8G,8C                                                                              9G,9C                                                                              6G,5C                                                                              9G,9C6G,5E             Cocklebur                                                                              8G,5C                                                                              6G  6G  5G  6G  7G  5G,3H                                                                              5G  2G  --  3G  0   4G0                    Pigweed 10C 7G  7G,6C                                                                              3G  6G  0   --  --  --  --  --  --  10C7G,9E               Nutsedge                                                                               10E 10E 7G  5G  3G  0   10E 2G  3G  0   7G  0   3G0                    Cotton  9G,5H                                                                              9G,5H                                                                              3H,6G                                                                              0   9G,3H                                                                              7G,3H                                                                              3H,7G                                                                              3G  5G,5H                                                                              4G,3H                                                                              3G  0   8G2G                   Morningglory                                                                           8G,5C                                                                              7G,3C                                                                              7G,5H                                                                              3G  8G,3H                                                                              5G  7G,3H                                                                              3H  3G  4G  3G  3G  8G4G                   Cassia  5G  5G  4G  3G  5G  4G  7G,3C                                                                              3G  6G  6G  5G  0   8G0                    Teaweed 7G  5G  4G  3G  3G  2G  10E 3G  6G,3C                                                                              4G  2G  0   5G0                    Velvetleaf                                                                             9G,5C                                                                              8G,3H                                                                              6G,5H                                                                              4G,3H                                                                              2G  3G  7G,8C                                                                              5G,3H                                                                              5G,5H                                                                              4G,3H                                                                              5G,3H                                                                              0   6G0                    Jimsonweed                                                                             9G,8C                                                                              5G,3C                                                                              5G  2G  4G  3G  6G,3C                                                                              4G  4G,3C                                                                              3G  3G  0   7G,7C0                 Soybean 8G,5H                                                                              7G,5H                                                                              6G,5H                                                                              2H  5G,1C                                                                              2G  5G,3H                                                                              2G  3G  4G  2G  0   00                     Rice    10E 10E 7G  5G  0   0   10E 10E 10E 7G  7G,7C                                                                              3G  8G,3H 6G               Wheat   7G  7G,3C                                                                              4G  2G  0   0   4G  0   3G  3G  2G  0   360                    __________________________________________________________________________

Test C

Twenty-five cm diameter plastic pots filled with Fallsington silt loam were planted with soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria sp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). Approximately 21/2 weeks after planting, the young plants and the soil around them were sprayed overall with the test chemicals dissolved in a non-phytotoxic solvent. Two weeks after treatment, all species were compared to untreated controls and visually rated for response to treatment. The rating system was as described previously for Test A. The data are presented in Table C. Note that one compound is especially tolerant to alfalfa.

    TABLE C       POST-EMERGENCE Over-the-Top Soil/Foliage Treatment        Compound 5 Compound 7 Compound 8 Compound 11 Compound 13 Compound 15      Compound 16 Compound 17 Rate kg/ha 0.06 0.0125 0.06 0.0125 0.06 0.125      0.06 0.125 0.006 0.06 0.125 0.06 0.125 0.006 .063 .016 .250 .063        Soybeans 10G,7C 8G,5C 10G,8C 10G,3C 9G,6C 10G,5C 10C 8G,5C 2C 9G,2C 5G      10G,7C 10G,3C 6G 8G 8G 9G 6G Velvetleaf 9G,8C 6G 10C 9G 10C 7G 10C 10C 0      9G,4C 2G,2C 9G,8C 5G,2C 6G 9G,7C 8G,4C 9G,9C 7G,5C Sesbania 9G,3C 7G      9G,3C 8G 10C 8G 10C 10C 4G 8G 2G 9G,9C 5G 7G 8G 7G,5C 9G,8C 7G,2C Cassia      9G,3C 3G 8G 4G 8G 5C 9G,9C 9G,9C 2C 2C 0 9G,8C 9G,6C 0 2C 3G,2C 9G,7C      9G,7C Cotton 8G 6G 10G 7G 10G 9G,5C 9G,9C 9G,9C 2C 8G 2G 10G 8G,3C 6G 6G      2G 8G,3C 7G,2C Morningglory 9G 3G 9G,6C 8G 9G,9C 8G 9G,9C 9G,9C 2G 9G 4G      9G,5C 7G 7G 2G 0 9G,7C 8G,7C Alfalfa 9G,5C 2G 6G 9G 10C 8G 10C 10C 4G 3G      0 10C 9G 6G 2C 2C 10C 8G,7C Jimsonweed 0 0 9G 0 10C 7G 9G,4C 9G,2C 5G 0      2C 10C 4G 2G 5G 5G 7G 8G Cocklebur 0 0 8G 5G 8G 5G 9G 6G 0 5G 2C 8G 2G      4G 8G 7G 8G 8G Sunflower 4G 0 8G,2H 6G 8G 5G 9G,9C 7G 2C 4G 4G 10C 6G,2H      3G 5G 7G 8G,6C 4G,4C Mustard 9G 9G 9G,9C 9G 10C 9G 10C 10C 0 9G 7G 10C      8G 4G 10C 10C 9G,9C 9G,9C Sugarbeets 8G 5G,3C 8G 9G 10C 9G,8C 10C 9G,4C      3G 9G 4G 9G,9C 5G 6G 9G 9G 9G,5C 9G,5C Corn 8G,3U 8G,3U 9G,9U 9G,9C 10C      7G,3U 9G,9C 9C,3C 4G 8G,3U 8G,1H 7G,3U 6G 2G 9G,5C 9G,5C 10C 9G,9C      Crabgrass 0 4C 4G 0 0 0 2G 0 0 2G 0 0 0 3G 10C 7G 6G,3C 2G Rice 4G,2C 4G      7G,3C 7G,3C 6G,5C 4G 10C 9G,8C 0 8G 8G 0 0 0 7G,4C 7G,1C 9G,8C 7G      Nutsedge 8G 9C 7G 9C 10C 3G,3C 9G,9C 9G,9C 0 8G,7C 7G 0 0 3G 6G 4G 10C      9C Barnyardgrass 7G 5G 9G,9C 8G,8C 10C 8G 9G,8C 9G,2U 3G 9G,2H 6G 0 0 2G      9G,4C 10C 9G,8C 8G Wheat 0 0 9G,2C 5G 5G,2C 3G 7G,5U 6G,4C 0 7G,3C 5G 0      0 0 8G,2C 8G,4C 9G,4C 9G,2C Giant foxtail 0 0 8G 4G 9G 5G 9G,2U 8G 2G 6G      0 0 6G 0 8G 8G 8G,3C 8G Wild Oats 4G,4C 2C 9G,9C 7G 6G,2C 2G 10C 7G,2C 0      7G,3C 6G,2C 0 0 0 9G 8G,5C 9G,4C 8G Sorghum 7G 6G 8G,8C 7G,2U 7G 6G 10C      8G,6C 4G 7G 7G 4G 0 2G 10C 8G,8C 8G,9C 8G,8C Johnsongrass 5G 5G 9G,8C      9G,2U 10C 9G,3U -- -- 5G 9G,2U 4G 0 3G 3G 9G,7U 8G,7U 9G,8C 7G,3U Field      Bindweed 5G 4G 7G 0 10C 6G -- -- 2C 0 2G 10C 8G 0 5G -- 5G 2G        Compound 17 Compound 18 Compound 21 Compound 22 Compound 23 Rate kg/ha .      016 0.06 0.0125 0.006 0.006 0.06 0.0125 0.06 0.0125 0.006 0.006 0.06      0.0125        Soybeans 6G 10G,6C 8G 9G 5G 10C 10G,5C 10C 10C 10G,3C 10G,5C 10G,6C      8G,6C Velvetleaf 7G 9G 8G 5G 4G 9G,8C 6G 10C 8G,5C 7G,2C 10C 6G 2G      Sesbania 7G 9G 2G 4G 8G 9G,8C 6G 10C 10C 9G,8C 10G,6C 9G,5C 3G Cassia 6G      9G 5G,3C 0 0 8G 2G 8G 9G,8C 5G,3C 4G 8G,2C 7G Cotton 4G 9G,5C 2G 1C 5G      9G 3G 9G,5C 8G,2C 8G,2C 7G 9G,5C 7G Morningglory 8G,5C 3G 4G 0 4G 9G 0      9G,8C 9G,7C 8G,2C 8G 5G 4G Alfalfa 6G,3C 2G,2C 0 4G 0 9G,5C 0 9G,9C      7G,5C 8G,2C 6G 8G,6C 5G Jimsonweed 2G 9G 6G 8G,2C 0 7G 0 9G 9G 4G 3G 0 0      Cocklebur 4G 7G 6G 0 6G 8G 5G 8G 6G 4G 6G 3G 0 Sunflower 6G,2C 8G,2H 4G      0 2C 8G,1H 3G 8G 5G 5G 10C 6G 1G Mustard 7G,2C 9G,5C 8G 5G 2G 10C 8G 10C      7G 8G 7G,3C 6G 8G Sugarbeets 8G 9G,5C 8G 5G 6G 10C 9G 10C 10C 1G 9G 5G 0      Corn 9G,7C 8G,8C 8G,3C 8G,5H 6G,3H 10C 9G,7C 10C 10C 7G,8C 7G,3H 9G,5C      9G,3U Crabgrass 0 4G 0 0 0 7G 0 4G,2C 3G 0 4G 0 0 Rice 7G 9G,5C 7G 3G,2C      4G 10C 7G,7C 10C 8G,8C 5G,5C 7G 7G,3C 2G Nutsedge 2G 10C 10C 8G,2C 4G      7G,7C 5G,5C 10C 10C 7C 0 8G 3C Barnyardgrass 4G 9G,6C 10C 4G,2C 1G 10C      10C 10C 10C 6G,2C 7G,1H 10C 5G Wheat 2G 9G 6G 5G 1G 9G,8C 5G 8G,6C 8G,2C      2G 2G 1G 0 Giant foxtail 7G 8G 4G 0 4G 9G 8G 9G,2C 9G 2G 3G 4G 4G Wild      Oats 4G 9G,5C 5G 0 0 8G 6G 9G,8C 9G 2G 0 6G 1C Sorghum 7G 10C 7G,8C 6G      8G 10C 7G,3C 10C 8G,3C 8G 7G 8G,5C 6G Johnsongrass 4G 9G,8C 10C 5G,4U 5G      9G,8U 7G,3U 10C 10C 6G,4C 7G,2H 9G,2U 7G Field Bindweed 0 5G 0 0 0 10C      2G 6G 9G 7G 3G 2G 2C 

What is claimed is:
 1. A compound selected from ##STR120## wherein A is a six-membered aromatic heterocycle, a six-membered dihydroaromatic heterocycle or a six-membered tetrahydroaromatic heterocycle which contains 1-4 hetero-atoms selected from 0-1 oxygen atoms, 0-1 sulfur atoms, and/or 0-4 nitrogen atoms; the heterocycles may be optionally substituted with 1-4 CH₃, 1-3 OCH₃, 0-1 SCH₃, 0-1 Cl, 0-1 N(CH₃)₂, or 0-1 CN groups;R is H or CH₃ ; R₁ is H, F, Cl, Br, CH₃, OCH₃, CF₃ or NO₂ ; R₂ is H or CH₃ ; R₃ is H or CH₃ ; R₄ is ##STR121## X is CH₃, OCH₃ or Cl; Y is H, CH₃, C₂ H₅, OCH₃, OC₂ H₅, CH₂ OCH₃, NH₂, NHCH₃ or N(CH₃)₂ ; and Z is N; provided that(1) the bond between N--R and A is attached to to a nitrogen or carbon atom of A.
 2. Compounds of claim 1 wherein A is an unsubstituted or substituted six-membered aromatic heterocycle containing one to three nitrogen atoms.
 3. Compounds of claim 1 wherein A is an unsubstituted or substituted six-membered dihydroaromatic heterocycle containing two nitrogen atoms.
 4. Compounds of claim 1 wherein A is an unsubstituted or substituted six-membered tetrahydroaromatic heterocycle containing one nitrogen atom and optionally one heteroatom selected from nitrogen, oxygen or sulfur.
 5. Compounds of claim 4 wherein Y is CH₃ or OCH₃.
 6. Compounds of claim 5 wherein A is unsubstituted or optionally substituted with 0-4 CH₃ or 0-2 OCH₃ groups.
 7. Compounds of claim 6 wherein A is a pyridine, a pyrimidine or a 1,3,5-triazine.
 8. Compounds of claim 6 wherein A is a tetrahydropyrimidine, a tetrahydro-1,2-oxazine, a tetrahydro-1,3-oxazine, or a tetrahydro-1,3-thiazine.
 9. Compounds of claim 7 wherein R, R₁, R₂ and R₃ are H, and A is unsubstituted, or optionally substituted with one methyl group.
 10. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 11. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 12. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
 13. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
 14. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 1. 15. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 2. 16. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 3. 17. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 4. 